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

HRID 1636320Notes

Reaction equation

HRID 1636320 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:22])[CH2:18][O:19][CH2:20][CH3:21]>O1CCOCC1>[CH3:7][O:8][C:9]1[S:13][C:12](=[O:14])[N:11]([CH:18]([O:19][CH2:20][CH3:21])[C:17](=[O:22])[CH3:16])[N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1929405-Methoxy-1,3,4-thiadiazol-2(3H)-oneHCID 138062981-Chloro-3-ethoxypropan-2-one

Product 1

HCID 193507225-Methoxy-3-(1-ethoxy-2-oxopropyl)-3H-[1,3,4]thiadiazol-2-oneYield 85.4%

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 31 g of 1-chloro-3-ethoxypropan-2-one 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. 45 g of the title compound are thus obtained in the form of a light yellow oil.

Workup

  1. temperaturethe reaction mixture is heated to 60°
  2. filtrationat 20°, is filtered over Celite
  3. concentrationThe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-9a983f76c50b49cba7409d5ef3110da5
Source dataset
uspto-grants-2000_03
Patent number
US06034083

Reaction notes

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