Water → HCID 53699280, compound

HRID 1703720Notes

Reaction equation

HRID 1703720 reaction equation
[OH-].[Na+].O.[CH3:4][C@H:5]1[CH2:10][C@@H:9]([CH3:11])[CH2:8][N:7]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C:24]=2[Cl:25])[C:20]([O:22]C)=[O:21])(=[O:14])=[O:13])[CH2:6]1>CO>[CH3:4][C@H:5]1[CH2:10][C@@H:9]([CH3:11])[CH2:8][N:7]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C:24]=2[Cl:25])[C:20]([OH:22])=[O:21])(=[O:13])=[O:14])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54351328HCID 54351328, compound

Product 1

HCID 53699280HCID 53699280, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

An aqueous solution of 4.2 g. (105 m moles) of sodium hydroxide in 130 ml. of water is added to 18 g. (52.5 m moles) of methyl 5-(cis-3,5-dimethylpiperidinosulfonyl)-6-chlorobenzoate in 130 ml. of methanol, and resulting reaction mixture allowed to stir at 40° C. for 1 hr. The solution is poured into ice water (1.5 l.) and extracted several times with benzene. The aqueous phase is separated, acidified with 12N hydrochloric acid, and the precipitated product filtered and air dried, 17.3 g. Recrystallization from ethyl acetate-hexane gave the purified product, 16.4 g., m.p. 152.5°-153° C.

Workup

  1. customreaction mixture
  2. extractionextracted several times with benzene
  3. customThe aqueous phase is separated
  4. filtrationthe precipitated product filtered
  5. customair dried
  6. customRecrystallization from ethyl acetate-hexane
  7. customgave the purified product, 16.4 g

Sources & evidence

ORD record
ord-9e8a9cb62fdd456dbed522ebbdfc4f62
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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