Water → HCID 13914068, compound

HRID 1709706Notes

Reaction equation

HRID 1709706 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[S:7][CH2:8][C:9](=[O:11])[N:10]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)CC)C.O>C(Cl)Cl>[F:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[S:7][CH:8]=[C:9]([O:11][S:13]([CH3:12])(=[O:15])=[O:14])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23036576HCID 23036576, compound

Product 1

HCID 13914068HCID 13914068, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.2 g of 2-(3-fluoropropylthio)-1,3-thiazoline-4-one was dissolved in 80 ml of methylene chloride and cooled below 10° C. 5.5 g of methanesulfonyl chloride and 8.9 ml of triethylamine were added dropwise to the solution keeping the temperature below 15° C., followed by stirring at room temperature for 2 hours. After addition of water, the reaction mixture was extracted by methylene chloride, then organic layer is washed with water and dried over anhydrous sodium sulfate, followed by concentration to an oil, which is purified by silica-gel column chromatography to obtain 6.0 g of the objective compound as a pale brown oil (yield: 69.1%).

Workup

  1. temperaturecooled below 10° C
  2. customthe temperature below 15° C.
  3. extractionthe reaction mixture was extracted by methylene chloride
  4. washorganic layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration to an oil, which
  7. customis purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-091fe47357dc4f15bb3d1ca92107802a
Source dataset
uspto-grants-1990_08
Patent number
US04950679

Reaction notes

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