Thiophenol → 2-Acetylamino-4-methyl-5-phenylsulfanyl-thiophene-3-carboxylic acid amide

HRID 1049868Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[C:8]([CH3:13])[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2].[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([CH3:13])[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

Intermediate 6 (2-Acetylamino-5-chloro-4-methyl-thiophene-3-carboxylic acid amide) (1.16 g, 5 mmol) is mixed with benzenethiol (535 μL, 5.25 mmol) and Cs2CO3 (3.25 g, 10 mmol) in DMF (15 mL). The resulting mixture is stirred at 120° C. for 30 min, then diluted with water, affording a suspension which is left to stir at room temperature overnight. The solid is separated by filtration, the cake is dried, and the resulting solid is used as such.

Workup

customaffording a suspension which
waitis left
stirringto stir at room temperature overnight
customThe solid is separated by filtration
customthe cake is dried

Sources & evidence

ORD record: ord-4bc2203c4ec842c2bb7d53bb21dc4194
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382254B2

Reaction notes

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