Chloroacetone → 5-Methoxy-3-(2-oxopropyl)-3H-[1,3,4]thiadiazol-2-one

HRID 1957368Notes

Reaction equation

HRID 1957368 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.Cl[CH2:16][C:17](=[O:19])[CH3:18]>O1CCOCC1>[CH3:7][O:8][C:9]1[S:13][C:12](=[O:14])[N:11]([CH2:16][C:17](=[O:19])[CH3:18])[N:10]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 1929405-Methoxy-1,3,4-thiadiazol-2(3H)-one

Product 1

HCID 193507245-Methoxy-3-(2-oxopropyl)-3H-[1,3,4]thiadiazol-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

69 g of potassium carbonate are added to a solution of 33 g of 5-methoxy-3H-[1,3,4]thiadiazol-2-one in 400 ml of dioxane and the reaction mixture is heated to 60°. Then 21 g of chloroacetone 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. 45 g of crystals of the title compound having a melting point of 66°-67° 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-da81a45b56724a5caca92ca73ae4e203
Source dataset
uspto-grants-1998_07
Patent number
US05783704

Reaction notes

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