Benzenesulfonyl chloride → 2-Bromobenzoic acid 2-phenylsulfonylhydrazide

HRID 567438Notes

Reaction equation

HRID 567438 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-c54278cd9de94dcdb2f5ff0f39a37066
Source dataset
uspto-grants-2001_01
Patent number
USRE037029E1

Reaction notes

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