Water → HCID 13914027, compound

HRID 414252Notes

Reaction equation

HRID 414252 reaction equation
[CH2:1]([S:4][C:5]1[S:6][CH2:7][C:8](=[O:10])[N:9]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>C(#N)C>[CH2:1]([S:4][C:5]1[S:6][CH:7]=[C:8]([O:10][S:18]([CH3:17])(=[O:20])=[O:19])[N:9]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 13561056HCID 13561056, compound

Product 1

HCID 13914027HCID 13914027, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8 g of 2-n-propylthio-1,3-thiazoline-4-one and 4.8 g of anhydrous sodium carbonate were suspended in acetonitrile, followed by stirring. 7.9 g of methanesulfonyl chloride was added dropwise to the suspension below 10° C. After the addition, the reaction was continued under stirring at room temperature for 2 hours. The reaction solution was poured into water and extracted by ether. The ether layer was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. The oil obtained by concentration was purified by silica-gel column chromatography to 9.1 g of the objective compound as a yellow oil (yield: 78.8%)

Workup

  1. additionAfter the addition
  2. stirringunder stirring at room temperature for 2 hours
  3. extractionextracted by ether
  4. washThe ether layer was washed with a saturated aqueous solution of common salt
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe oil obtained by concentration

Sources & evidence

ORD record
ord-9db4a5be3bc74e5e9e3b59eac4f1ed9a
Source dataset
uspto-grants-1988_12
Patent number
US04791127

Reaction notes

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