Sodium hydride → HCID 86649766, compound

HRID 1880251Notes

Reaction equation

HRID 1880251 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][SH:6].Br[CH2:10][C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:29])([F:28])[F:27])[O:23][N:22]=2)=[CH:17][C:16]=1[Cl:39])=[O:12].[Cl-].[NH4+]>O1CCCC1>[Cl:39][C:16]1[CH:17]=[C:18]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:29])([F:27])[F:28])[O:23][N:22]=2)[CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][C:11](=[O:12])[CH2:10][S:6][CH2:5][C:4]([F:8])([F:7])[F:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 41339242,2,2-TrifluoroethanethiolHCID 86649767HCID 86649767, compound

Product 1

HCID 86649766HCID 86649766, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 0.0271 g of 55% oily sodium hydride in 2 mL of tetrahydrofuran, a solution of 0.0802 g of 2,2,2-trifluoroethanethiol and 0.20 g of 2-bromo-N-[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methylacetamide in 2 mL of tetrahydrofuran was added while stirring the suspension at 0° C., and the resultant mixture was stirred at room temperature for 10 minutes. After the completion of the reaction, 2 mL of a saturated ammonium chloride aqueous solution was added to the reaction mixture and the resultant mixture was extracted with ethyl acetate (3 mL×2). The organic phase was washed with water and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was purified by preparative medium pressure liquid chromatography eluting with ethyl acetate-hexane (a gradient from 1:9 to 1:3) using a medium pressure preparative apparatus (trade name: YFLC-Wprep; manufactured by Yamazen Corporation) to obtain 0.074 g of the objective substance as a colorless resinoid.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe resultant mixture was extracted with ethyl acetate (3 mL×2)
  3. washThe organic phase was washed with water
  4. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by preparative medium pressure liquid chromatography
  7. washeluting with ethyl acetate-hexane (a gradient from 1:9 to 1:3)
  8. customto obtain 0.074 g of the objective substance as a colorless resinoid

Sources & evidence

ORD record
ord-bc0986c955af4ba981eae15432107bdd
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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