Benzenesulfonyl chloride → 2-Bromobenzoic acid 2-phenylsulfonylhydrazide

HRID 1459735Notes

Reaction equation

HRID 1459735 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:12]1([S:18]([NH:7][NH:6][C:4](=[O:5])[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[Br:1])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 1014602-Bromobenzohydrazide

Product 1

HCID 77099642-Bromobenzoic acid 2-phenylsulfonylhydrazide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-bromobenzoic acid hydrazide (132 g) in pyridine (1.2 L) cooled to about 10 C. with an ice bath, was added benzensulfonyl chloride (78.3 ml). After complete addition, the reaction was stirred at ambient temperature for four hours, and then poured into ice-hydrochloric acid to precipitate a yellow solid, 135 g. The material was recrystallized from isopropanol to yield 125 g of 2-bromobenzoic acid 2-phenylsulfonylhydrazide, m.p.=154°-156° C.

Workup

  1. additionAfter complete addition
  2. customto precipitate a yellow solid, 135 g
  3. customThe material was recrystallized from isopropanol

Sources & evidence

ORD record
ord-294ad1426cd24733ba79a23e1ac4674f
Source dataset
uspto-grants-1998_12
Patent number
US05854243

Reaction notes

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