No renderable structure data available
C1=CC=C(C(=C1)CNC(=O)CC#N)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-[(2-chlorophenyl)methyl]-2-cyanoacetamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 64488-07-9 |
| Database ID | 964628 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-[(2-chlorophenyl)methyl]-2-cyanoacetamide (CAS 64488-07-9) 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 964628
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-9c287c7f45f54bf7b16e62da41f9efb8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: As for Example 1, N-o-chlorobenzyl-2-cyanoacetamide, colorless needles, m.p. 108°-109° C., (prepared as described in U.S. Pat. No. 3,116,312) is heated with N,N-dimethylformamide dimethylacetal to give N-o-chlorobenzyl-2-cyano-3-dimethylaminoacrylamide as colorless needles, m.p. 144°-146.5° C.
Source ID: ord-4689c073e6f64cfeb4f105905c23a081Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C=O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g
Source ID: ord-4b9d7d3c2eb2469780a26cac38d754f3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C=O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g
Source ID: ord-4b9d7d3c2eb2469780a26cac38d754f3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.;ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C=O);δ8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO). at reflux for 2 hours The solvent is removed in vacuo the residue is recrystallized from ether/pentane to give 56 g
Source ID: ord-64b6f6c055f349e0a67860281b62bdfcConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9c287c7f45f54bf7b16e62da41f9efb8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C= O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g
Source ID: ord-f5fcc6b6a2c044b5b79258fd54dffa1dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C= O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g
Source ID: ord-f5fcc6b6a2c044b5b79258fd54dffa1dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.; ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C= O); δ 8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO). at reflux for 2 hours The solvent is removed in vacuo the residue is recrystallized from ether/pentane to give 56 g
Source ID: ord-da769fed3e944d6c9fa8c28ef1e2136cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: As for Example 1, N-o-chlorobenzyl-2-cyanoacetamide, colorless needles, m.p. 108°-109° C., (prepared as described in U.S. Pat. No. 3,116,312) is heated with N,N-dimethylformamide dimethylacetal to give N-o-chlorobenzyl-2-cyano-3-dimethylaminoacrylamide as colorless needles, m.p. 144°-146.5° C.
Source ID: ord-4689c073e6f64cfeb4f105905c23a081Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C=O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g
Source ID: ord-4b9d7d3c2eb2469780a26cac38d754f3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.;ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C=O);δ8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO). at reflux for 2 hours The solvent is removed in vacuo the residue is recrystallized from ether/pentane to give 56 g
Source ID: ord-64b6f6c055f349e0a67860281b62bdfcPubChem References
These sources are listed in the compound's public database record.
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