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

HRID 1703704Notes

Reaction equation

HRID 1703704 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. 185°-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. 185°-187° C.

Sources & evidence

ORD record
ord-333476c5d3d8459f88660b9af3263a1c
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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