Benzoic acid, 2-chloro-5-(chlorosulfonyl)- → 2-Chloro-5-(2-[p-chlorophenyl)ethylaminosulfonyl)benzoic Acid

HRID 1730588Notes

Reaction equation

HRID 1730588 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([NH:24][CH2:23][CH2:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-HCID 674302-(4-Chlorophenyl)ethylamine

Product 1

HCID 205058642-Chloro-5-(2-[p-chlorophenyl)ethylaminosulfonyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-chlorosulfonyl benzoic acid, 3.5 g. (0.014 mole), is added to a solution of 2-(p-chlorophenyl)ethylamine, 6.5 g. (0.042 mole) in 25 ml. methylene chloride. The resulting slurry is stirred overnight and filteredto recover 9.7 g. of residue. This is recrystallized three times from aqueous isopropanol, then dissolved in 1N aqueous sodium hydroxide, washedthree times with ether, and then acidified with conc. hydrochloric acid. The resulting precipitate is recrystallized twice from aqueous isopropanolto yield the desired product, m.p. 176°- 178° C.

Workup

  1. customfilteredto recover 9.7 g
  2. customThis is recrystallized three times from aqueous isopropanol
  3. dissolutiondissolved in 1N aqueous sodium hydroxide
  4. customThe resulting precipitate is recrystallized twice from aqueous isopropanolto

Sources & evidence

ORD record
ord-8acde20ce0ea4566a5ea95a7c4bd389b
Source dataset
uspto-grants-1976_11
Patent number
US03992441

Reaction notes

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