Dimethyl Sulfate → HCID 13322356, compound

HRID 1982280Notes

Reaction equation

HRID 1982280 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([NH:6][C:7](=[O:21])[C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([N:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([NH:6][C:7](=[O:21])[C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH3:24])[S:15]([N:18]([CH3:20])[CH3:19])(=[O:16])=[O:17])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 13322327N-(4-Chlorophenyl)-4-[(dimethylsulfamoyl)amino]benzamide

Product 1

HCID 13322356HCID 13322356, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 300 mg of 4'-chloro-4-[(dimethylaminosulfonyl)amino]benzanilide 7, 140 mg of potassium carbonate, 130 mg of dimethyl sulfate 8, and 10 ml of dried acetone is refluxed for 30 minutes. Acetone is distilled off from the reaction mixture, the residue is basified with 10% sodium hydroxide solution and extracted with methylene chloride. The organic layer is washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue is crystallized from ethyl acetate-isopropyl ether to give 300 mg of 4'-chloro-4-[methyl(dimethylaminosulfonyl)amino]benzanilide 9 as crystals, m.p. 155°-156° C.

Workup

  1. temperatureis refluxed for 30 minutes
  2. distillationAcetone is distilled off from the reaction mixture
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-1c369b3d02594e71adb41949ae25eb86
Source dataset
uspto-grants-1986_06
Patent number
US04595780

Reaction notes

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