Dimethyl Sulfate → HCID 12790655, compound

HRID 1155279Notes

Reaction equation

HRID 1155279 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:23])[C:10]1[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]=[CH:12][C:11]=1[O:21][CH3:22])[CH2:4][CH3:5])[CH3:2].S(OC)(O[CH3:28])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:23])[C:10]1[CH:15]=[C:14]([N:16]([CH3:28])[S:17]([CH3:20])(=[O:18])=[O:19])[CH:13]=[CH:12][C:11]=1[O:21][CH3:22])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 12790645HCID 12790645, compound

Product 1

HCID 12790655HCID 12790655, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-(diethylaminoethyl)-5-methanesulfonamido-2-methoxybenzamide in acetone are added dimethyl sulfate and potassium carbonate. The resultant mixture is refluxed for 2 hours. After evaporating the solvent, the residue is mixed with water and shaken with methylene chloride. The organic layer is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuum. The residue is washed with isopropyl ether to give N-(diethylaminoethyl)-2-methoxy-5-(N-methyl-methanesulfonamido)benzamide as crystals melting at 48°-50° C.

Workup

  1. customAfter evaporating the solvent
  2. additionthe residue is mixed with water
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuum
  6. washThe residue is washed with isopropyl ether

Sources & evidence

ORD record
ord-124fdd2022d6420db3d2eab11c29c2e6
Source dataset
uspto-grants-1981_11
Patent number
US04301159

Reaction notes

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