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Hydrochloric Acid → 2-Benzylamino-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606602
Notes
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Reaction equation

HRID 1606602 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:15])[C:5](=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:6]([OH:8])=[O:7].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.Cl>[OH-].[Na+]>[CH2:16]([NH:15][C:4]1[CH:3]=[C:2]([Cl:1])[C:10]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7498Benzyl BromideHCID 221015002-Amino-4-chloro-5-methylsulphonylbenzoic acid

Product 1

HCID 215439572-Benzylamino-4-chloro-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 14798
Sodium Hydroxide
Solvent
2×

Procedure

A solution of 4-chloro-5-methylsulfonylanthranilic acid (250 mg.) and benzyl bromide (180 mg.) in 5% aqueous sodium hydroxide is heated on a water bath at 50° C. for four hours during which time 5% aqueous sodium hydroxide is added a few drops at a time to maintain a basic reaction medium. The reaction mixture is poured into water and acidified with hydrochloric acid to give 2-benzylamino-4-chloro-5-methylsulfonylbenzoic acid, m.p. 179° C. after recrystallization from ethanol and water.

Workup

  1. additionis added a few drops at a time
  2. temperatureto maintain a basic reaction medium

Sources & evidence

ORD record
ord-127b8276f602473ea10c613a83e5db3c
Source dataset
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03953476

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes