5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → N-(4-bromo-3-methyl-5-isoxazolyl)-5-chloro-3-methylbenzo[b]thiophene-2-sulfonamide

HRID 234297Notes

Reaction equation

HRID 234297 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[C:3]=1[Br:8].[Cl:9][C:10]1[CH:23]=[CH:22][C:13]2[S:14][C:15]([S:18](Cl)(=[O:20])=[O:19])=[C:16]([CH3:17])[C:12]=2[CH:11]=1>>[Br:8][C:3]1[C:4]([CH3:7])=[N:5][O:6][C:2]=1[NH:1][S:18]([C:15]1[S:14][C:13]2[CH:22]=[CH:23][C:10]([Cl:9])=[CH:11][C:12]=2[C:16]=1[CH3:17])(=[O:20])=[O:19]

Participants

3

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 104875194-Bromo-3-methylisoxazol-5-amine

Product 1

HCID 15342060N-(4-bromo-3-methyl-5-isoxazolyl)-5-chloro-3-methylbenzo[b]thiophene-2-sulfonamideYield 18%

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-5-chloro-3-methylbenzo[b]thiophene-2-sulfonamide was prepared in the same manner as described in Example 2 from 5-amino-4-bromo-3-methylisoxazole and 5-chloro-3-methylbenzo[b]thiophene-2-sulphonyl chloride in 18% yield. Purification was achieved by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 153°-155° C.

Workup

  1. customPurification
  2. customwas achieved by recrystallization from ethyl acetate/hexanes
  3. customto give a crystalline solid, m.p. 153°-155° C.

Sources & evidence

ORD record
ord-6bf843ca87bc4c52b087c6f6af96f670
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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