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

HRID 1390492Notes

Reaction equation

HRID 1390492 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 filtered to recover 9.7 g. of residue. This is recrystallised three times from aqueous isopropanol, then dissolved in 1N aqueous sodium hydroxide, washed three times with ether, and then acidified with conc. hydrochloric acid. The resulting precipitate is recrystallized twice from aqueous isopropanol to yield the desired product, m.p. 176°-178° C.

Workup

  1. filtrationfiltered
  2. customto recover 9.7 g
  3. customThis is recrystallised three times from aqueous isopropanol
  4. dissolutiondissolved in 1N aqueous sodium hydroxide
  5. washwashed three times with ether
  6. customThe resulting precipitate is recrystallized twice from aqueous isopropanol

Sources & evidence

ORD record
ord-040324d9a1974f9caa74de638142b223
Source dataset
uspto-grants-1979_02
Patent number
US04138399

Reaction notes

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