Benzoyl isocyanate → N-(2-cyano-5-methoxyphenylcarbamoyl)benzamide

HRID 44386Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:12]([N:20]=[C:21]=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:2]=1[NH:1][C:21]([NH:20][C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:22])#[N:5]

Participants

Reactant 2

HCID 78210Benzoyl isocyanate

HCID 37231282-Amino-4-methoxybenzonitrile

Product 1

HCID 57456926N-(2-cyano-5-methoxyphenylcarbamoyl)benzamide

Procedure

Prepared as in Example 53a from 2-amino-4-methoxybenzonitrile and benzoyl isocyanate as white solid (99 mg, 45%). 1H NMR (400 MHz, DMSO-d6) δ3.86 (s, 3H), 6.87 (dd, J=2.5 Hz, 2.4 Hz, 1H), 7.54 (t, J=8 Hz, 2H), 7.66 (t, J=1.2 Hz, 1H), 7.77 (d, J=7.2 Hz, 1H), 7.89 (d, J=8.4 Hz, 1H), 8.03 (d, J=2.8 Hz, 2H), 11.35 (s, 1H), 11.52 (s, 1H). MS 295 (MH+).

Sources & evidence

ORD record: ord-fc0def11d86b4397a9c960d2719d7423
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541421B2

Reaction notes

Loading…