Diethyl Sulfate → HCID 22818969, compound

HRID 1154308Notes

Reaction equation

HRID 1154308 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]([N:24]3[CH:28]=[CH:27][N:26]=[CH:25]3)[C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.S(OCC)(O[CH2:33][CH3:34])(=O)=O>O.CS(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16]/[C:17](/[N:24]3[CH:28]=[CH:27][N:26]=[CH:25]3)=[C:18](/[O:23][CH2:33][CH3:34])\[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6163Diethyl SulfateHCID 14797Potassium HydroxideHCID 20434993HCID 20434993, compound

Product 1

HCID 22818969HCID 22818969, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

6 g of potassium hydroxide, dissolved in a little water, are added dropwise to 36.85 g (0.1 mole) of 1-(4'-chloro-4-biphenylyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one in 50 ml of dimethylsulphoxide. The mixture is subsequently stirred for a short time and 16 g (0.11 mole) of diethyl sulphate are then added dropwise. During this addition, the temperature of the reaction mixture is kept at about 40° C. and thereafter it was kept at 80° C. for 1/2 hour. It was allowed to cool, water is added and the crystalline precipitate is filtered off and recrystallised from petroleum ether. 22 g (50% of theory) of (E)-1-(4'-chloro-4-biphenylyloxy)-3,3-dimethyl-2-ethoxy-1-(imidazol-1-yl)-1-butene of melting point of 112°-113° C. are obtained.

Workup

  1. additionare then added dropwise
  2. additionDuring this addition
  3. customis kept at about 40° C.
  4. temperatureto cool
  5. filtrationthe crystalline precipitate is filtered off
  6. customrecrystallised from petroleum ether

Sources & evidence

ORD record
ord-0aad7f92a3084132b916c0c587172c60
Source dataset
uspto-grants-1984_12
Patent number
US04489085

Reaction notes

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