Dimethyl Sulfate → HCID 20505957, compound

HRID 1730596Notes

Reaction equation

HRID 1730596 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 heatedfor 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 thecourse 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 ethy 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. customof the reaction
  2. temperatureto maintain basicity
  3. washthe reaction mixture is washed with ether
  4. customdecanted from the precipitated gum
  5. dissolutionThe gum is dissolved in ethy acetate
  6. customchromatographed on a silica gel column
  7. customConcentration of the column fraction yields the product, m.p. 170°-174° C.

Sources & evidence

ORD record
ord-5f898a59d42b4565a745dbdab2286542
Source dataset
uspto-grants-1976_11
Patent number
US03992441

Reaction notes

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