Benzoic acid, 2-chloro-5-(chlorosulfonyl)- → HCID 20505867, compound

HRID 355129

Reaction equation

HRID 355129 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 20505867HCID 20505867, compound

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 1 N 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 1 N 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-37bfdf2cf16e4d66871ca50ca34985de
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Linked notes

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