4-Nitrobenzenesulfonyl chloride → 2-Thiophenesulfonamide

HRID 1258369Notes

Reaction equation

HRID 1258369 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH2:9])(=[O:8])=[O:7].[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:9])(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH2:9])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 728812-Thiophenesulfonamide

Product 2

HCID 227844-NitrobenzenesulfonamideHCID 728812-ThiophenesulfonamideYield 96.6%

Procedure

4-nitrobenzenesulfonamide was prepared according to the procedure for thiophene-2-sulfonamide YG1-030 except using 4-nitrobenzenesulfonyl chloride, which afforded the title compound 1.953 g (96.6%) as a pale yellow solid, m.p.: 178-180° C. 1H-NMR, 400 MHz, d6-DMSO, δ (ppm): 8.40 (d, J=8.6 Hz, 2H), 8.04 (d, J=8.6 Hz, 2H), 7.72 (br, 2H). HRMS (ESI-ve) m/z calculated for C6H6N2O4S (M−H)− 200.9976. Found 200.9986.

Sources & evidence

ORD record
ord-3b11d11450674294b59702368e9ed290
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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