Hydride → HCID 15676020, compound

HRID 1646565Notes

Reaction equation

HRID 1646565 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([CH:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:20]([F:30])[CH:19]=3)[CH3:17])[N:15]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li].[H-]>O1CCCC1>[F:30][C:20]1[CH:19]=[C:18]([CH:16]([C:14]2[N:15]=[C:11]([NH:10][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:12][CH:13]=2)[CH3:17])[CH:23]=[CH:22][C:21]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 166653HydrideHCID 3028194LithiumHCID 15676043HCID 15676043, compound

Product 1

HCID 15676020HCID 15676020, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-phenylacetamido-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (1.00 g, 2.51 mmol) in tetrahydrofuran (20 ml) was added lithium aluminu hydride (150 mg) by portion, then the mixture was refluxed for 2 hr. After cooling, the reaction mixture was filterated and evaporated under reduced pressure to a residue. The residue was extracted with chloroform and the extracts were washed with water, dried, then evaporated under reduced pressure to a residue, which chromatographed and recrystallized to afford 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-phenethylaminothiazole (504 mg, 50% yield): mp 74.5°-75.5° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hr
  2. temperatureAfter cooling
  3. customevaporated under reduced pressure to a residue
  4. extractionThe residue was extracted with chloroform
  5. washthe extracts were washed with water
  6. customdried
  7. customevaporated under reduced pressure to a residue, which
  8. customchromatographed
  9. customrecrystallized

Sources & evidence

ORD record
ord-1d1200e81c3b4661befdcbad8be83412
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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