Benzenesulfonyl chloride → 2-Bromobenzoic acid 2-phenylsulfonylhydrazide

HRID 1461824Notes

Reaction equation

HRID 1461824 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 (1.21), cooled to about 10° C. with an ice bath, was added benzenesulfonyl chloride (78.3 ml). After complete addition, the reaction was stirred at ambient temperature for 4 hours, and then poured into ice-HCl to precipitate a solid (135 g). The solid 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 solid (135 g)
  3. customThe solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-d124fdd5922c4ee9868990ae6cbb4674
Source dataset
uspto-grants-1991_12
Patent number
US05077405

Reaction notes

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