Ethyl isocyanate → Methyl N-(ethylcarbamoyl)benzenecarboximidate

HRID 1827843Notes

Reaction equation

[CH3:1][O:2][C:3](=[NH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([N:13]=[C:14]=[O:15])[CH3:12]>>[CH2:11]([NH:13][C:14]([N:10]=[C:3]([O:2][CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:15])[CH3:12]

Participants

Reactant 2

HCID 8022Ethyl isocyanate

HCID 345018Methyl benzimidate

Product 1

HCID 69416768Methyl N-(ethylcarbamoyl)benzenecarboximidateYield 95.1%

Conditions

Temperature: 50 °C

Procedure

A neat mixture of benzimidic acid methyl ester (750 mg, 5.56 mmol) and ethyl isocyanate (808 mg, 11.3 mmol) was stirred at 50° C. for 24 h. Excess isocyanate was removed under vacuum to provide the desired product as a colorless viscous oil (1.09 g, 95%). This material was used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.07 (t, J=7.3 Hz, 3H), 3.25 (q, J=7.3 Hz, 2H), 3.87 (s, 3H), 4.97 (br s, 1), 7.26–7.40 (m, 2H), 7.45 (d, J=7.4 Hz, 1H), 7.69–7.71 (m, 2H). MS, m/z 207=M+1.

Workup

customExcess isocyanate was removed under vacuum

Sources & evidence

ORD record: ord-8a28a7df7ea64620a64dc88cafd49982
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056915B2

Reaction notes

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