Dimethyl Sulfate → HCID 20505957, compound

HRID 1390503Notes

Reaction equation

HRID 1390503 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]([OH:21])[CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].S(OC)(O[CH3:28])(=O)=O>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]([O:21][CH3:28])[CH2:15]2)(=[O:12])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium Hydroxide2×HCID 20506088HCID 20506088, compound

Product 1

HCID 20505957HCID 20505957, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-5-(3,4-dihydroxypiperidinosulfonyl)benzoic acid (4.0 g.) is heated for 16 hours at 90° C. with water (15 ml.), NaOH (1.0 g. and dimethyl sulfate (0.5 ml.). Dimethyl sulfate and NaOH are added during the course of the reaction to maintain basicity. After cooling to room temperature, the reaction mixture is washed with ether and the aqueous phase is acidified with concentrated hydrochloric acid and decanted from the precipitated gum. The gum is dissolved in ethyl acetate and chromatographed on a silica gel column. The product fractions in the column effluent are identified by paper chromatography, with development in a solvent system of ethyl acetate-acetic acid. Concentration of the column fraction yields the product, m.p. 170°-174° C.

Workup

  1. temperatureto maintain basicity
  2. washthe reaction mixture is washed with ether
  3. customdecanted from the precipitated gum
  4. dissolutionThe gum is dissolved in ethyl acetate
  5. customchromatographed on a silica gel column
  6. customConcentration of the column fraction yields the product, m.p. 170°-174° C.

Sources & evidence

ORD record
ord-cbb8d96cd9f7409aabce6020ef5d8dd3
Source dataset
uspto-grants-1979_02
Patent number
US04138399

Reaction notes

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