Water → HCID 13914034, compound

HRID 414253Notes

Reaction equation

HRID 414253 reaction equation
[CH:1]([S:4][C:5]1[S:6][CH2:7][C:8](=[O:10])[N:9]=1)([CH3:3])[CH3:2].[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C.O>C(Cl)Cl>[CH:1]([S:4][C:5]1[S:6][CH:7]=[C:8]([O:10][S:12]([CH3:11])(=[O:14])=[O:13])[N:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23036575HCID 23036575, compound

Product 1

HCID 13914034HCID 13914034, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8 g of 2-isopropylthio-1,3-thiazoline-4-one was dissolved in 100 ml of methylene chloride and cooled below 10° C. Then, 7.8 g of methanesulfonyl chloride and 12.6 ml of triethylamine were added dropwise to the solution below 15° C. with attention to out-break of heat. After that, the reaction was continued with stirring at room temperature for 2 hours. Water was added to the reaction mixture and extracted by ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. The oil obtained by concentration was purified by silica-gel column chromatography to obtain 9.1 g of the objective compound as a pale brown crystal (yield: 78.8%).

Workup

  1. temperaturecooled below 10° C
  2. temperatureof heat
  3. extractionextracted by ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe oil obtained by concentration
  7. customwas purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-f908f3058d70447abe92494a48d5cc43
Source dataset
uspto-grants-1988_12
Patent number
US04791127

Reaction notes

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