Benzoyl isothiocyanate → N-benzoyl-N'-(2-cyanophenyl)thiourea

HRID 711605Notes

Reaction equation

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

Participants

Reactant 2

HCID 68284Benzoyl isothiocyanate

HCID 2799732-Amino-6-methylbenzonitrile

Product 1

HCID 909209N-benzoyl-N'-(2-cyanophenyl)thiourea

Procedure

Prepared as in example 1a from 2-amino-6-methylbenzonitrile and benzoyl isothiocyanate as a pale-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (m, 1H), 7.52-7.69 (m, 5H), 7.98-8.01 (m, 2H), 11.99 (s, 1H), 12.54 (s, 1H). MS 296 (MH+).

Sources & evidence

ORD record: ord-21ac780120db4846bd22f20b0efae65b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

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