2-Nitro-4-toluonitrile → 4-Methyl-2-nitro-thiobenzamide

Reaction equation

C(N)(=[S:8])C1C=CC=CC=1.[CH3:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=1.CC1C=CC(C(N)=O)=C([N+]([O-])=O)C=1>>[CH3:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]([NH2:16])=[S:8])=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=1

Participants

Reactant 3

HCID 962352-Nitro-4-toluonitrile

HCID 683563Thiobenzamide

HCID 132443694-Methyl-2-nitrobenzamide

Product 1

HCID 541688084-Methyl-2-nitro-thiobenzamideYield 98%

Procedure

The thio-benzamide, was prepared as described in Example 14-1, starting from 4-methyl-2-nitro-benzonitrile via 4-methyl-2-nitro-benzamide which gave the title compound (1.03 g, 98%). LC/MS: (Method I): tR=0.54 min, >80%, m/z (ESI)=180 (M-NH2)+.

Sources & evidence

ORD record: ord-9395df17e5504ab898cab1de46807b6f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666834B2

Reaction notes

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