No renderable structure data available
CC(=O)N=C=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | acetyl isocyanate |
|---|---|
| IUPAC Name | — |
| CAS Number | 3998-25-2 |
| Database ID | 12300404 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
acetyl isocyanate (CAS 3998-25-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 12300404
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-610ec5b219044a608d3805c051b27b51Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (25.18 g, 50.0 mmol), acetyl isocyanate (8.50 ml, 9.53 g, 112 mmol), and dioxane (250 ml) was refluxed under nitrogen for 5 hours, cooled and concentrated in vacuo to a yellow foam. The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride: acetone; 9:1; v:v to give four products; the 3-methyl-Δ3 -cephem; starting sulfoxide, the title penam, and the cepham (in order of elution). The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g). Re-chromatography of a portion gave an analytical sample: m.p. 83°-85°; nmr 100 MHz (CDCl3) ppm 8.40 (1, s, ##STR59## 8.20 (2, d, J=8.5, 1/2 aromatic AB pNB), 7.56 (3, d, J=8.5 over m, 1/2 AB, pNB and C6 -NH), 7.5 (2, m) and 6.9 (3, m, O-Ph-H's), 5.7 (2, m's, C5 -C6 -H's), 5.32 (2, br, s, pNB methylene), 4.88 (1, s, C3 -H), 4.56 (2, s, ##STR60## 4.26 and 4.06 (2, d's, J=11.5 AB of C2 -CH2O), 2.22 (3, s, ##STR61## and 1.47 (3, s, C2 -CH3); nmr 13C 4 carbonyls ca 170 ppm, carbamate carbonyl C 157.0, C2 singlet at 67.4, while C2 -CH2O is t at 72.3, and C2 -CH3 is q at 21.7. cooled concentrated in vacuo to a yellow foam The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride v:v to give four products The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g) Re-chromatography of a portion gave an analytical sample
Source ID: ord-263a2d44f5824d4a9ceb3c5313d4e20cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (25.18 g, 50.0 mmol), acetyl isocyanate (8.50 ml, 9.53 g, 112 mmol), and dioxane (250 ml) was refluxed under nitrogen for 5 hours, cooled and concentrated in vacuo to a yellow foam. The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride: acetone; 9:1; v:v to give four products; the 3-methyl-Δ3 -cephem; starting sulfoxide, the title penam, and the cepham (in order of elution). The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g). Re-chromatography of a portion gave an analytical sample: m.p. 83°-85°; nmr 100 MHz (CDCl3) ppm 8.40 (1, s, ##STR59## 8.20 (2, d, J=8.5, 1/2 aromatic AB pNB), 7.56 (3, d, J=8.5 over m, 1/2 AB, pNB and C6 -NH), 7.5 (2, m) and 6.9 (3, m, O-Ph-H's), 5.7 (2, m's, C5 -C6 -H's), 5.32 (2, br, s, pNB methylene), 4.88 (1, s, C3 -H), 4.56 (2, s, ##STR60## 4.26 and 4.06 (2, d's, J=11.5 AB of C2 -CH2O), 2.22 (3, s, ##STR61## and 1.47 (3, s, C2 -CH3); nmr 13C 4 carbonyls ca 170 ppm, carbamate carbonyl C 157.0, C2 singlet at 67.4, while C2 -CH2O is t at 72.3, and C2 -CH3 is q at 21.7. cooled concentrated in vacuo to a yellow foam The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride v:v to give four products The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g) Re-chromatography of a portion gave an analytical sample
Source ID: ord-263a2d44f5824d4a9ceb3c5313d4e20cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-(3,5-Dichlorophenylthio)-4-isoproyl-1-(4-pyridylmethyl)-2-hydroxymethyl-1H-imidazole (89) (245 mg, 0.6 mmol) prepared in accordance with the method as described in WO 96/10019 was converted to the carbamate with acetyl isocyanate (5 eq.) in the same manner as the example 66 to give the compound 90 (225 mg, 76%) as crystals. Mp. 135-137° C. Rf 0.32 (10:1 EtOAc - CH3OH).
Source ID: ord-06b7f5f2e4d54f3ab5491022a5be57ecConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (4.85 g, 10.0 mmol) and acetyl isocyanate (2.3 ml, 30 mmol) in dioxane (50 ml) was refluxed under nitrogen for 7 hours. The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride:acetone; 9:1, v:v. Two major bands were eluted; the first was the Δ3 3-methylcephem (28%, 1.29 g) and the second was the title compound obtained in 45% yield (2.56 g) as an off-white foam: mp 83°-85°; nmr 100 MHz (CDCl3) ppm 8.24 (2, d, J=9 Hz, 1/2 aromatic AB pNB), 7.61 (2, d, J=9, 1/2 pNB AB), 7.28 (5, s, phenyl), 5.54 (2, m's, C6 --C5 --H's), 5.40 (2, br s, pNB methylene), 4.91 (1, s, C3 --H), 4.27 1, d, J=12, 1/2 C2 --CHHO AB), 4.08 (1, d, J=12, 1/2 C2 --methylene AB), 3.12 ##STR73## 2.12 (3, s, acetyl), and 1.41 (3, s, C2 --CH3). The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride Two major bands were eluted obtained in 45% yield (2.56 g) as an off-white foam
Source ID: ord-0afdc3ad1115418992f71dc165b57d20Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (4.85 g, 10.0 mmol) and acetyl isocyanate (2.3 ml, 30 mmol) in dioxane (50 ml) was refluxed under nitrogen for 7 hours. The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride:acetone; 9:1, v:v. Two major bands were eluted; the first was the Δ3 3-methylcephem (28%, 1.29 g) and the second was the title compound obtained in 45% yield (2.56 g) as an off-white foam: mp 83°-85°; nmr 100 MHz (CDCl3) ppm 8.24 (2, d, J=9 Hz, 1/2 aromatic AB pNB), 7.61 (2, d, J=9, 1/2 pNB AB), 7.28 (5, s, phenyl), 5.54 (2, m's, C6 --C5 --H's), 5.40 (2, br s, pNB methylene), 4.91 (1, s, C3 --H), 4.27 1, d, J=12, 1/2 C2 --CHHO AB), 4.08 (1, d, J=12, 1/2 C2 --methylene AB), 3.12 ##STR73## 2.12 (3, s, acetyl), and 1.41 (3, s, C2 --CH3). The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride Two major bands were eluted obtained in 45% yield (2.56 g) as an off-white foam
Source ID: ord-0afdc3ad1115418992f71dc165b57d20Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (25.18 g, 50.0 mmol), acetyl isocyanate (8.50 ml, 9.53 g, 112 mmol), and dioxane (250 ml) was refluxed under nitrogen for 5 hours, cooled and concentrated in vacuo to a yellow foam. The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride: acetone; 9:1; v:v to give four products; the 3-methyl-Δ3 -cephem; starting sulfoxide, the title penam, and the cepham (in order of elution). The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g). Re-chromatography of a portion gave an analytical sample: m.p. 83°-85°; nmr 100 MHz (CDCl3) ppm 8.40 ##STR60## 8.20 (2, d, J=8.5, 1/2 aromatic AB pNB), 7.56 (3, d, J=8.5 over m, 1/2 AB, pNB and C6 --NH), 7.5 (2, m) and 6.9 (3, m, O--Ph--H's), 5.7 (2, m's, C5 -C6 --H's), 5.32 (2, br s, pNB methylene), 4.88 (1, s, C3 --H), 4.56 ##STR61## 4.26 and 4.06 (2, d's, J=11.5, AB of C2 --CH2O), 2.22 ##STR62## and 1.47 (3, s, C2 --CH3); nmr 13C 4 carbonyls ca 170 ppm, carbamate carbonyl C 157.0, C2 singlet at 67.4, while C2 --CH2O is t at 72.3, and C2 --CH3 is q at 21.7. cooled concentrated in vacuo to a yellow foam The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride v:v to give four products The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g) Re-chromatography of a portion gave an analytical sample
Source ID: ord-d87fd03ee8574b158f515bee0f8ff049Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (25.18 g, 50.0 mmol), acetyl isocyanate (8.50 ml, 9.53 g, 112 mmol), and dioxane (250 ml) was refluxed under nitrogen for 5 hours, cooled and concentrated in vacuo to a yellow foam. The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride: acetone; 9:1; v:v to give four products; the 3-methyl-Δ3 -cephem; starting sulfoxide, the title penam, and the cepham (in order of elution). The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g). Re-chromatography of a portion gave an analytical sample: m.p. 83°-85°; nmr 100 MHz (CDCl3) ppm 8.40 ##STR60## 8.20 (2, d, J=8.5, 1/2 aromatic AB pNB), 7.56 (3, d, J=8.5 over m, 1/2 AB, pNB and C6 --NH), 7.5 (2, m) and 6.9 (3, m, O--Ph--H's), 5.7 (2, m's, C5 -C6 --H's), 5.32 (2, br s, pNB methylene), 4.88 (1, s, C3 --H), 4.56 ##STR61## 4.26 and 4.06 (2, d's, J=11.5, AB of C2 --CH2O), 2.22 ##STR62## and 1.47 (3, s, C2 --CH3); nmr 13C 4 carbonyls ca 170 ppm, carbamate carbonyl C 157.0, C2 singlet at 67.4, while C2 --CH2O is t at 72.3, and C2 --CH3 is q at 21.7. cooled concentrated in vacuo to a yellow foam The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride v:v to give four products The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g) Re-chromatography of a portion gave an analytical sample
Source ID: ord-d87fd03ee8574b158f515bee0f8ff049Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (4.85 g, 10.0 mmol) and acetyl isocyanate (2.3 ml, 30 mmol) in dioxane (50 ml) was refluxed under nitrogen for 7 hours. The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride:acetone; 9:1, v:v. Two major bands were eluted; the first was the Δ3 3-methylcephem (28%, 1.29 g) and the second was the title compound obtained in 45% yield (2.56 g) as an off-white foam: mp 83°-85°; nmr 100 MHz (CDCl3) ppm 8.24 (2, d, J=9 Hz, 1/2 aromatic AB pNB), 7.61 (2, d, J=9, 1/2 pNB AB), 7.28 (5, s, phenyl), 5.54 (2, m's C6 --C5 --H's), 5.40 (2, br s, pNB methylene), 4.91 (1, s, C3 --H), 4.27 1, d, J=12, 1/2 C2 --CHHO AB), 4.08 (1, d, J=12, 1/2 C2 -methylene AB), 3.12 (2, s, ##STR72## 2.12 (3, s, acetyl), and 1.41 (3, s, C2 --CH3). The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride Two major bands were eluted obtained in 45% yield (2.56 g) as an off-white foam
Source ID: ord-6a4d4c1ff299487a888ac37536bd5436Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (25.18 g, 50.0 mmol), acetyl isocyanate (8.50 ml, 9.53 g, 112 mmol), and dioxane (250 ml) was refluxed under nitrogen for 5 hours, cooled and concentrated in vacuo to a yellow foam. The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride:acetone; 9:1; v:v to give four products; the 3-methyl-Δ3 -cephem; starting sulfoxide, the title penam, and the cephem (in order of elution). The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g). Re-chromatography of a portion gave an analytical sample: m.p. 83°-85°; nmr 100 MHz (CDCl3) ppm 8.40 (1,s, ##STR59## 8.20 (2, d, J=8.5, 1/2 aromatic AB pNB), 7.56 (3, d, J=8.5 over m, 1/2 AB, pNB and C6 --NH), 7.5 (2, m) and 6.9 (3, m, O--Ph--H's), 5.7 (2, m's, C5 --C6 --H's), 5.32 (2, br s, pNB methylene), 4.88 (1, s, C3 --H), 4.56 (2, s, ##STR60## 4.26 and 4.06 (2, d's,J=11.5, AB of C2 --CH2O), 2.22 (3, s, ##STR61## and 1.47 (3, s, C2 --CH3); nmr 13C 4 carbonyls ca 170 ppm, carbamate carbonyl C 157.0, C2 singlet at 67.4, while C2 --CH2O is t at 72.3, and C2 --CH3 is q at 21.7. cooled concentrated in vacuo to a yellow foam The foam was chromatographed on silica gel (1.7 Kg) with methylene chloride v:v to give four products The penam fractions were concentrated to a colorless foam in 40.2% yield (11.80 g) Re-chromatography of a portion gave an analytical sample
Source ID: ord-6b8319b7638b4a5d8fc19c4aa342417eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound (13 mg, 51%) was prepared starting from the product of Example 2 and methylformyl isocyanate using the method described in Example 4; MS(ES) m/e 474 [M+H]+.
Source ID: ord-0b83f3114e454a5eb9760a27ae50a871Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (1S,3S,5R,6R) 2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid-1-oxide p-nitrobenzyl ester (4.85 g, 10.0 mmol) and acetyl isocyanate (2.3 ml, 30 mmol) in dioxane (50 ml) was refluxed under nitrogen for 7 hours. The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride:acetone; 9:1, v:v. Two major bands were eluted; the first was the Δ3 3-methylcephem (28%, 1.29 g) and the second was the title compound obtained in 45% yield (2.56 g) as an off-white foam: mp 83°-85°; nmr 100 MHz (CDCl3) ppm 8.24 (2, d, J=9 Hz, 1/2 aromatic AB pNB), 7.61 (2, d, J=9, 1/2 pNB AB), 7.28 (5, s, phenyl), 5.54 (2, m's, C6 --C5 --H's), 5.40 (2, br s, pNB methylene), 4.91 (1, s, C3 --H), 4.27 1, d, J=12, 1/2 C2 --CHHO AB), 4.08 (1, d, J=12, 1/2 C2 --methylene AB), 3.12 ##STR73## 2.12 (3, s, acetyl), and 1.41 (3, s, C2 --CH3). The light orange solution was concentrated in vacuo to a foam which was chromatographed on silica gel (500 g) with methylene chloride Two major bands were eluted obtained in 45% yield (2.56 g) as an off-white foam
Source ID: ord-0afdc3ad1115418992f71dc165b57d20PubChem References
These sources are listed in the compound's public database record.
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