Potassium Carbonate → 3-(2-Cyclopropyl-2-oxo-ethyl)-5-methoxy-3H-[1,3,4]thiadiazol-2-one

HRID 1957367Notes

Reaction equation

HRID 1957367 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[S:13][C:12](=[O:14])[NH:11][N:10]=1.[CH:15]1([C:18]([CH2:20]Br)=[O:19])[CH2:17][CH2:16]1>O1CCOCC1>[CH:15]1([C:18](=[O:19])[CH2:20][N:11]2[N:10]=[C:9]([O:8][CH3:7])[S:13][C:12]2=[O:14])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1929405-Methoxy-1,3,4-thiadiazol-2(3H)-oneHCID 109208412-Bromo-1-cyclopropylethan-1-one

Product 1

HCID 193507253-(2-Cyclopropyl-2-oxo-ethyl)-5-methoxy-3H-[1,3,4]thiadiazol-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

55 g of potassium carbonate are added to a solution of 26.4 g of 5-methoxy-3H-[1,3,4]-thiadiazol-2-one in 700 ml of dioxane and the reaction mixture is heated to 60°. Then 35 g of bromomethyl cyclopropyl ketone are added dropwise within a short period of time and the reaction mixture is stirred at 70° for 20 hours and then, at 20°, is filtered over Celite. The filtrate is concentrated by evaporation. The residue is stirred with diisopropyl ether and filtered with suction. 41 g of crystals of the title compound having a melting point of 98°-100° are thus obtained.

Workup

  1. temperaturethe reaction mixture is heated to 60°
  2. filtrationat 20°, is filtered over Celite
  3. concentrationThe filtrate is concentrated by evaporation
  4. stirringThe residue is stirred with diisopropyl ether
  5. filtrationfiltered with suction
  6. customare thus obtained

Sources & evidence

ORD record
ord-0d1d4a3f87a743eea0e8268d26ea284b
Source dataset
uspto-grants-1998_07
Patent number
US05783704

Reaction notes

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