Water → HCID 86593199, compound

HRID 2356733Notes

Reaction equation

HRID 2356733 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:16]3[CH:20]=[CH:19][S:18][CH:17]=3)=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C.O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:16]3[CH:20]=[CH:19][S:18][CH:17]=3)=[C:11]([CH2:13][CH2:14][O:15][S:22]([CH3:21])(=[O:24])=[O:23])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13583383HCID 13583383, compound

Product 1

HCID 86593199HCID 86593199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, to a solution of 2-(4-fluoro-phenyl)-4-(2-hydroxyethyl)-5-(3-thienyl)oxazole (300 mg) in methylene chloride (10 ml) were successively added methane-sulfonyl chloride (96 μl) and triethylamine (188 μl) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water and extracted with methylene chloride. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to obtain a crude product of 2-(4-fluorophenyl)-4-(2-methanesulfonyloxyethyl)-5-(3-thienyl)oxazole.

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e85db56655354fd1990f8592fe1459e3
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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