Dimethyl Sulfate → HCID 21279524, compound

HRID 2291218Notes

Reaction equation

HRID 2291218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][S:10]([C:13]1[N:14]=[C:15]2[S:20][CH:19]=[C:18]([CH3:21])[N:16]2[N:17]=1)(=[O:12])=[O:11].[CH3:22]C(C)([O-])C.[K+].S(OC)(OC)(=O)=O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH3:22])[S:10]([C:13]1[N:14]=[C:15]2[S:20][CH:19]=[C:18]([CH3:21])[N:16]2[N:17]=1)(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 21279525HCID 21279525, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21279524HCID 21279524, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 1 (3 g) in dimethylformamide (20 ml) was added potassium t-butoxide (1.1 g) with cooling and stirring. Dimethyl sulphate (0.92 ml) was added dropwise, and the reaction mixture was stirred overnight. Addition to ice/water/ether and filtration, followed by recrystallisation from ethyl acetate gave 1.9 g of the desired product, mp 178°-180° C.

Workup

  1. temperaturewith cooling
  2. stirringthe reaction mixture was stirred overnight
  3. additionAddition
  4. filtrationto ice/water/ether and filtration
  5. customfollowed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-a73cc618cdae4e94a0a9aec650859c91
Source dataset
uspto-grants-1989_01
Patent number
US04795483

Reaction notes

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