Acetone → HCID 15676073, compound

HRID 1646576Notes

Reaction equation

HRID 1646576 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([CH:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:22]([F:32])[CH:21]=2)[CH3:19])[N:17]=1)=[S:11])(=O)C1C=CC=CC=1.CC(C)=O.CO.C(=O)([O-])[O-].[K+].[K+]>O>[F:32][C:22]1[CH:21]=[C:20]([CH:18]([C:16]2[N:17]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[S:14][CH:15]=2)[CH3:19])[CH:25]=[CH:24][C:23]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 11430Potassium CarbonateHCID 15676067HCID 15676067, compound

Product 1

HCID 15676073HCID 15676073, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-benzoyl-N'-(4-(1-(2-fluoro-4-biphenylyl) ethyl)thiazol-2-yl)thiourea (0.25 g, 0.561 mmol) in mixture of acetone (10 ml) and methanol (2.5 ml) was added potassium carbonate (0.05 g) in water (1 ml). After the mixture was refluxed for 5 h, the mixture was extracted with ethyl acetate. The extracts were washed with water, dried over, and evaporated under reduced pressure to residue, which was chromatographed and recrystallized with mixture of chloroform and n-hexane to afford N-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea (0.172 g, 82% yield) as crystalline material: 192.0°-194.0° C.

Workup

  1. temperatureAfter the mixture was refluxed for 5 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extracts were washed with water
  4. customdried over, and
  5. customevaporated under reduced pressure to residue, which
  6. customwas chromatographed
  7. customrecrystallized with mixture of chloroform and n-hexane

Sources & evidence

ORD record
ord-7a319e27b4954e578b96c342a587e8da
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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