Acetic Acid → 2-Amino-4-chloro-5-methylsulphonylbenzoic acid

HRID 1606601Notes

Reaction equation

HRID 1606601 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.C(O)(=O)C.[NH3:21]>>[Cl:11][C:9]1[CH:10]=[C:2]([NH2:21])[C:3](=[CH:7][C:8]=1[S:12]([CH3:15])(=[O:14])=[O:13])[C:4]([OH:6])=[O:5]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 313Hydrochloric AcidHCID 2210136551521-75-6

Product 1

HCID 221015002-Amino-4-chloro-5-methylsulphonylbenzoic acidYield 64%

Procedure

A solution of 2,4-dichloro-5-methylsulfonylbenzoic acid (Example 1, Step B) (60 g.; 0.267 mole) in aqueous ammonia (28%, 900 ml.) is heated in an autoclave at 180° C. for 12 hours. The cooled reaction mixture is poured into ice (3 kg.) and concentrated hydrochloric acid (1.3 liters) which causes the product to precipitate 42 g. (64% yield) of 4-chloro-5-methylsulfonylanthranilic acid, m.p. 286.5°-288.5° C. after recrystallization from acetic acid.

Workup

  1. customThe cooled reaction mixture
  2. customto precipitate 42 g

Sources & evidence

ORD record
ord-89553a0a77644821ac61ea07f63ae0c6
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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