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

HRID 1703695Notes

Reaction equation

HRID 1703695 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 recrystallized 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 recrystallized 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-366cbb9b5b524f819c9ef1125544c0fb
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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