Dimethyl Sulfate → HCID 12848777, compound

HRID 1065036Notes

Reaction equation

HRID 1065036 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:25])[C:11]1[CH:16]=[C:15]([NH:17][S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:14]=[CH:13][C:12]=1[O:23][CH3:24])[CH3:2].[CH3:26]OS(OC)(=O)=O>CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:25])[C:11]1[CH:16]=[C:15]([N:17]([CH3:26])[S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:14]=[CH:13][C:12]=1[O:23][CH3:24])[CH3:2]

Participants

5

Reactant 2

HCID 6497Dimethyl SulfateHCID 12848760HCID 12848760, compound

Product 1

HCID 12848777HCID 12848777, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-ethanesulfonamidobenzamide (266 mg) in dry acetone (7 ml), potassium carbonate and dimethylsulfate (100 mg) are added, and the resultant mixture is refluxed for 30 minutes. After evaporating the acetone, the residue is mixed with water and shaken with methylene chloride. The organic layer is washed with water, dried over sodium sulfate, and evaporated to remove the solvent. The residue is dissolved in methylene chloride, and the resultant mixture is chromatographed on a column of alumina, which is eluted with methylene chloride. After evaporating the eluate to remove the methylene chloride, the residue is washed with isopropyl ether and recrystallized from ethyl acetate/isopropyl ether in that order to give N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-(N-methylethanesulfonamido)benzamide (74 mg) as crystals melting at 85° to 87° C.

Workup

  1. customAfter evaporating the acetone
  2. additionthe residue is mixed with water
  3. washThe organic layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. dissolutionThe residue is dissolved in methylene chloride
  8. customthe resultant mixture is chromatographed on a column of alumina, which
  9. washis eluted with methylene chloride
  10. customAfter evaporating the eluate
  11. customto remove the methylene chloride
  12. washthe residue is washed with isopropyl ether
  13. customrecrystallized from ethyl acetate/isopropyl ether in that order

Sources & evidence

ORD record
ord-9630d7c12e4240538c0c455268ac0a68
Source dataset
uspto-grants-1982_05
Patent number
US04328155

Reaction notes

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