Benzoyl isocyanate → N-(3-Cyanothiophen-2-ylcarbamoyl)benzamide

Reaction equation

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

Participants

Reactant 2

HCID 78210Benzoyl isocyanate

HCID 7366072-Aminothiophene-3-carbonitrile

Product 1

HCID 57456909N-(3-Cyanothiophen-2-ylcarbamoyl)benzamide

Procedure

Prepared as in Example 1a from 2-aminothiophene-3-carbonitrile and benzoyl isocyanate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ7.23-7.19 (m, 2H), 7.55 (t, J=8.0 Hz, 2H), 7.70-7.66 (m, 1H), 8.04-8.02 (m, 2H), 11.62 (bs, 1H), 12.18 (bs, 1H). MS 272 (MH+).

Sources & evidence

ORD record: ord-aaa32e6826d44096a93eb47d72bc88d2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541421B2

Reaction notes

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