Benzoic acid, 2-chloro-5-(chlorosulfonyl)- → 2-Chloro-5-(4-hydroxymethylpiperidinosulfonyl)benzoic acid

HRID 1390500Notes

Reaction equation

HRID 1390500 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].[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]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 4207714-Piperidinemethanol

Product 1

HCID 205058672-Chloro-5-(4-hydroxymethylpiperidinosulfonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-chlorosulfonylbenzoic acid (5.0 g.) is added to a solution of 4-piperidyl carbinol (6.9 g.) in 40 ml. of methylene chloride. The solution is refluxed for 2 hours, cooled to room temperature and stirred overnight. The solution is evaporated to dryness, the gummy residue dissolved in 1N sodium hydroxide, and the alkaline solution extracted twice with ether. The aqueous solution is acidified with concentrated hydrochloric acid, and the precipitate recovered by filtration. Recrystallization from ethyl acetate yields crystals, m.p. 184°-187° C.

Workup

  1. temperatureThe solution is refluxed for 2 hours
  2. customThe solution is evaporated to dryness
  3. dissolutionthe gummy residue dissolved in 1N sodium hydroxide
  4. extractionthe alkaline solution extracted twice with ether
  5. filtrationthe precipitate recovered by filtration
  6. customRecrystallization from ethyl acetate
  7. customyields crystals, m.p. 184°-187° C.

Sources & evidence

ORD record
ord-e8b02bf8c0144b0f9858a7cd63f3acba
Source dataset
uspto-grants-1979_02
Patent number
US04138399

Reaction notes

Loading…