2,4-Dichlorobenzenethiol → 2-(2,4-Dichlorophenyl)sulfanyl-5-methylsulfonyl-3-nitro-thiophene

HRID 1192051Notes

Reaction equation

HRID 1192051 reaction equation
Br[C:2]1[S:3][C:4]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[SH:22]>>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[S:22][C:2]1[S:3][C:4]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8]

Participants

3

Reactant 2

HCID 707302,4-DichlorobenzenethiolHCID 602073102-Bromo-5-methanesulfonyl-3-nitrothiophene

Product 1

HCID 469321462-(2,4-Dichlorophenyl)sulfanyl-5-methylsulfonyl-3-nitro-thiopheneYield 25%

Procedure

Prepared by a similar procedure to that described as in Step D for example 22 from the 2-bromo-5-methylsulfonyl-3-nitro-thiophene (148 mg, 0.52 mmol) and 2,4-dichlorobenzenethiol (100 mg, 0.56 mmol) to afford the title product as a solid (50 mg, 25% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.35 (1H, s), 8.10 (1H, m), 8.20 (1H, m), 7.74 (1H, m), 3.42 (3H, s). MS m/z: 381.81 [M+H]+.

Workup

  1. customPrepared by a similar procedure to that

Sources & evidence

ORD record
ord-63ed1969cba34546b7e47c6814407508
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

Loading…