Water → HCID 117974116, compound

HRID 2272915Notes

Reaction equation

HRID 2272915 reaction equation
[H-].[Na+].Br[C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][C:12]=2[N:13]=1.[CH2:25]([SH:27])[CH3:26].[OH2:28].CN1C(=[O:35])CCC1>>[CH2:25]([S:27]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][C:12]=2[N:13]=1)(=[O:35])=[O:28])[CH3:26]

Participants

6

Reactant 5

HCID 962WaterHCID 6343EthanethiolHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 117974135HCID 117974135, compound

Product 1

HCID 117974116HCID 117974116, compound

Procedure

0.06 g of sodium hydride (60%) was added to 5 ml of a solution of 0.53 g of 2-(3-bromothiophen-2-yl)-5-pentafluoroethylbenzoxazole and 0.1 ml of ethanethiol in NMP at 0° C., and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous hydrochloric acid solution and a saturated aqueous salt solution, and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. To a mixture of the residue and 5 ml of chloroform was added 0.66 g of 3-chloroperoxybenzoic acid (purity of 65% or more), under ice cooling, and the mixture was stirred at room temperature for 1 hour. A 10% aqueous sodium thiosulfate solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.32 g of 2-(3-ethylsulfonylthiophen-2-yl)-5-pentafluoroethylbenzoxazole (Compound of Present Invention (35)).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a 10% aqueous hydrochloric acid solution
  3. dry with materiala saturated aqueous salt solution, and dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo a mixture of the residue and 5 ml of chloroform
  6. additionwas added 0.66 g of 3-chloroperoxybenzoic acid (purity of 65% or more)
  7. stirringunder ice cooling, and the mixture was stirred at room temperature for 1 hour
  8. additionA 10% aqueous sodium thiosulfate solution was poured into the reaction mixture
  9. extractionthe mixture was extracted with chloroform
  10. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b3198a8c6144dd1a41d0475d48c4ad7
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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