No renderable structure data available
CCOC(=O)CCCCCN=C=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ethyl 6-isocyanatohexanoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 5100-36-7 |
| Database ID | 3445675 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ethyl 6-isocyanatohexanoate (CAS 5100-36-7) 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 3445675
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5509ca88766147738c4ea2317764819eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5509ca88766147738c4ea2317764819eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5509ca88766147738c4ea2317764819eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diisopropylethylamine (35 μL, 0.2 mmol), 6-isocyanato-hexanoic acid ethyl ester (40 μL, 0.2 mmol), and {[4-(4′-amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 220: step b) 20 mg, 0.04 mmol) were stirred for 24 h in DCM (1 mL). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) and was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL). The solution was dried, concentrated in vacuo, and purified by SiO2 preparative TLC to yield the product (12 mg, 43%). 1H-NMR (CDCl3): δ 8.06 (s, 1H), 7.94 (m, 1H), 7.81 (m, 1H), 7.46 (m, 2H), 7.23 (br t, 1H, J=5.4 Hz), 7.15 (m, 1H), 7.07 (m, 2H), 6.97 (m, 1H), 5.32 (br t, 1H), 4.15 (q, 2H, J=7.2 Hz), 2.40 (s, 3H), 2.30 (t, 2H, J=7.3 Hz), 2.11 (s, 3H), 1.54–1–70 (m, 4H), 1.51 (s, 9H) 1.35 (m, 2H), 1.25 (t, 3H, J=7.3 Hz). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL) The solution was dried concentrated in vacuo purified by SiO2 preparative TLC
Source ID: ord-d0ce0a1be6af47e7ab64a228bdd05e7bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diisopropylethylamine (35 μL, 0.2 mmol), 6-isocyanato-hexanoic acid ethyl ester (40 μL, 0.2 mmol), and {[4-(4′-amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 220: step b) 20 mg, 0.04 mmol) were stirred for 24 h in DCM (1 mL). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) and was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL). The solution was dried, concentrated in vacuo, and purified by SiO2 preparative TLC to yield the product (12 mg, 43%). 1H-NMR (CDCl3): δ 8.06 (s, 1H), 7.94 (m, 1H), 7.81 (m, 1H), 7.46 (m, 2H), 7.23 (br t, 1H, J=5.4 Hz), 7.15 (m, 1H), 7.07 (m, 2H), 6.97 (m, 1H), 5.32 (br t, 1H), 4.15 (q, 2H, J=7.2 Hz), 2.40 (s, 3H), 2.30 (t, 2H, J=7.3 Hz), 2.11 (s, 3H), 1.54–1–70 (m, 4H), 1.51 (s, 9H) 1.35 (m, 2H), 1.25 (t, 3H, J=7.3 Hz). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL) The solution was dried concentrated in vacuo purified by SiO2 preparative TLC
Source ID: ord-d0ce0a1be6af47e7ab64a228bdd05e7bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Isocyanato-hexanoic acid ethyl ester (370 μL, 2.16 mmol) was added to a solution of 4-bromo-3-methyl-5-nitro-phenylamine (250 mg, 1.08 mmol, Example 135: step a) in CH2Cl2 (5 mL, anhydrous) at rt. The reaction mixture was stirred overnight, then diluted in EtOAc and washed with saturated NH4Cl solution, water, and brine. The organic layer was dried over magnesium sulfate. Removal of solvents in vacuo was followed by flash chromatography (50–75% EtOAc/hexanes) to afford the title compound as a brown oil (162 mg, 36%). 1H-NMR (CDCl3): δ 7.59 (d, 1H, J=2.56 Hz), 7.42–7.48 (m, 1H), 4.10–4.17 (m, 2H), 3.20–3.28 (m, 2H), 2.39 (s, 3H), 2.29–2.35 (m, 2H), 1.47–1.68 (m, 4H), 1.23–1.41 (m, 5H). at rt washed with saturated NH4Cl solution, water, and brine The organic layer was dried over magnesium sulfate Removal of solvents in vacuo
Source ID: ord-7bd146f7cb64447fbac0d743ba700855Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diisopropylethylamine (35 μL, 0.2 mmol), 6-isocyanato-hexanoic acid ethyl ester (40 μL, 0.2 mmol), and {[4-(4′-amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 220: step b) 20 mg, 0.04 mmol) were stirred for 24 h in DCM (1 mL). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) and was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL). The solution was dried, concentrated in vacuo, and purified by SiO2 preparative TLC to yield the product (12 mg, 43%). 1H-NMR (CDCl3): δ 8.06 (s, 1H), 7.94 (m, 1H), 7.81 (m, 1H), 7.46 (m, 2H), 7.23 (br t, 1H, J=5.4 Hz), 7.15 (m, 1H), 7.07 (m, 2H), 6.97 (m, 1H), 5.32 (br t, 1H), 4.15 (q, 2H, J=7.2 Hz), 2.40 (s, 3H), 2.30 (t, 2H, J=7.3 Hz), 2.11 (s, 3H), 1.54–1–70 (m, 4H), 1.51 (s, 9H) 1.35 (m, 2H), 1.25 (t, 3H, J=7.3 Hz). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL) The solution was dried concentrated in vacuo purified by SiO2 preparative TLC
Source ID: ord-1e70e3c6d632427bb2248c2cf2b336b4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Isocyanato-hexanoic acid ethyl ester (370 μL, 2.16 mmol) was added to a solution of 4-bromo-3-methyl-5-nitro-phenylamine (250 mg, 1.08 mmol, Example 135: step a) in CH2Cl2 (5 mL, anhydrous) at rt. The reaction mixture was stirred overnight, then diluted in EtOAc and washed with saturated NH4Cl solution, water, and brine. The organic layer was dried over magnesium sulfate. Removal of solvents in vacuo was followed by flash chromatography (50–75% EtOAc/hexanes) to afford the title compound as a brown oil (162 mg, 36%). 1H-NMR (CDCl3): δ 7.59 (d, 1H, J=2.56 Hz), 7.42–7.48 (m, 1H), 4.10–4.17 (m, 2H), 3.20–3.28 (m, 2H), 2.39 (s, 3H), 2.29–2.35 (m, 2H), 1.47-1.68 (m, 4H), 1.23–1.41 (m, 5H). at rt washed with saturated NH4Cl solution, water, and brine The organic layer was dried over magnesium sulfate Removal of solvents in vacuo
Source ID: ord-116d2ddf25c4447c865f011b180c3abfConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Isocyanato-hexanoic acid ethyl ester (370 μL, 2.16 mmol) was added to a solution of 4-bromo-3-methyl-5-nitro-phenylamine (250 mg, 1.08 mmol, Example 135: step a) in CH2Cl2 (5 mL, anhydrous) at rt. The reaction mixture was stirred overnight, then diluted in EtOAc and washed with saturated NH4Cl solution, water, and brine. The organic layer was dried over magnesium sulfate. Removal of solvents in vacuo was followed by flash chromatography (50–75% EtOAc/hexanes) to afford the title compound as a brown oil (162 mg, 36%). 1H-NMR (CDCl3): δ 7.59 (d, 1H, J=2.56 Hz), 7.42–7.48 (m, 1H), 4.10–4.17 (m, 2H), 3.20–3.28 (m, 2H), 2.39 (s, 3H), 2.29–2.35 (m, 2H), 1.47-1.68 (m, 4H), 1.23–1.41 (m, 5H). at rt washed with saturated NH4Cl solution, water, and brine The organic layer was dried over magnesium sulfate Removal of solvents in vacuo
Source ID: ord-116d2ddf25c4447c865f011b180c3abfConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diisopropylethylamine (35 μL, 0.2 mmol), 6-isocyanato-hexanoic acid ethyl ester (40 μL, 0.2 mmol), and {[4-(4′-amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 220: step b) 20 mg, 0.04 mmol) were stirred for 24 h in DCM (1 mL). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) and was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL). The solution was dried, concentrated in vacuo, and purified by SiO2 preparative TLC to yield the product (12 mg, 43%). 1H-NMR (CDCl3): δ 8.06 (s, 1H), 7.94 (m, 1H), 7.81 (m, 1H), 7.46 (m, 2H), 7.23 (br t, 1H, J=5.4 Hz), 7.15 (m, 1H), 7.07 (m, 2H), 6.97 (m, 1H), 5.32 (br t, 1H), 4.15 (q, 2H, J=7.2 Hz), 2.40 (s, 3H), 2.30 (t, 2H, J=7.3 Hz), 2.11 (s, 3H), 1.54–1–70 (m, 4H), 1.51 (s, 9H) 1.35 (m, 2H), 1.25 (t, 3H, J=7.3 Hz). The solution was partitioned between EtOAc (40 mL) and 0.1 N HCl (10 mL) was washed with additional 0.1N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL) The solution was dried concentrated in vacuo purified by SiO2 preparative TLC
Source ID: ord-d0ce0a1be6af47e7ab64a228bdd05e7bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-Isocyanato-hexanoic acid ethyl ester (370 μL, 2.16 mmol) was added to a solution of 4-bromo-3-methyl-5-nitro-phenylamine (250 mg, 1.08 mmol, Example 135: step a) in CH2Cl2 (5 mL, anhydrous) at rt. The reaction mixture was stirred overnight, then diluted in EtOAc and washed with saturated NH4Cl solution, water, and brine. The organic layer was dried over magnesium sulfate. Removal of solvents in vacuo was followed by flash chromatography (50–75% EtOAc/hexanes) to afford the title compound as a brown oil (162 mg, 36%). 1H-NMR (CDCl3): δ 7.59 (d, 1H, J=2.56 Hz), 7.42–7.48 (m, 1H), 4.10–4.17 (m, 2H), 3.20–3.28 (m, 2H), 2.39 (s, 3H), 2.29–2.35 (m, 2H), 1.47–1.68 (m, 4H), 1.23–1.41 (m, 5H). at rt washed with saturated NH4Cl solution, water, and brine The organic layer was dried over magnesium sulfate Removal of solvents in vacuo
Source ID: ord-7bd146f7cb64447fbac0d743ba700855PubChem References
These sources are listed in the compound's public database record.
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