4-(Methylthio)benzylamine → 5-((3,5-dichloropyridin-4-yl)thio)-N-(4-(methylthio)benzyl)-4-nitrothiophene-2-carboxamide

HRID 1192272Notes

Reaction equation

HRID 1192272 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14](Cl)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[CH3:21][S:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:28][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([S:22][CH3:21])=[CH:24][CH:25]=2)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 27600804-(Methylthio)benzylamineHCID 602073375-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carbonyl chloride

Product 1

HCID 602074965-((3,5-dichloropyridin-4-yl)thio)-N-(4-(methylthio)benzyl)-4-nitrothiophene-2-carboxamide

Procedure

Prepared according to the procedure described for example 70 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carbonyl chloride (200 mg, 0.54 mmol) from above and 4-methylthiobenzylamine (99.0 mg, 0.65 mmol). The title compound was obtained as a solid (100 mg, 19% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.35 (1H, m), 8.98 (2H, s), 8.46 (1H, s), 7.22 (4H, m), 4.35 (2H, m), 2.34 (3H, s). MS m/z: 484.11, 486.14 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-eb0e05369489469b81f6cd7736d427ec
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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