Hydrochloric Acid → 3-Benzylamino-4-chloro-5-methylsulfonyl benzoic acid

HRID 1606618Notes

Reaction equation

HRID 1606618 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([NH2:15])[C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>[OH-].[Na+].O>[CH2:16]([NH:15][C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 189525243-Methylsulfonyl-4-chloro-5-aminobenzoic acid

Product 1

HCID 215439813-Benzylamino-4-chloro-5-methylsulfonyl benzoic acid

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-methylsulfonyl-4-chloro-5-aminobenzoic acid (1.25 g.) in 1N sodium hydroxide (5 ml.) is added benzyl bromide (1 ml.). The stirred reaction is heated at 45°-50° C. for 6 hours with the occasional addition of a few drops of 1N sodium hydroxide to maintain a pH of 9. The reaction mixture is diluted with water (50 ml.) and acidified with 1N hydrochloric acid to give 0.9 g. (53 %) of 3-benzylamino-4-chloro-5-methylsulfonylbenzoic acid, m.p. 254°-256.5° C. after recrystallization from nitromethane.

Workup

  1. customThe stirred reaction
  2. temperatureto maintain a pH of 9
  3. customto give 0.9 g
  4. custom(53 %) of 3-benzylamino-4-chloro-5-methylsulfonylbenzoic acid, m.p. 254°-256.5° C. after recrystallization from nitromethane

Sources & evidence

ORD record
ord-4c4490632b944823a7a64f67bd3c6a41
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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