Phenyl Isothiocyanate → N-phenyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea

HRID 2072738Notes

Reaction equation

HRID 2072738 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1.[C:22]1([N:28]=[C:29]=[S:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O.C(=O)([O-])O.[Na+]>[C:22]1([NH:28][C:29]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[C:11]([F:21])[CH:10]=3)[CH3:8])[N:6]=2)=[S:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 7673Phenyl Isothiocyanate2×HCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

Product 1

HCID 15676065N-phenyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thioureaYield 16%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (0.50 g, 1.68 mmol) in acetone (10 ml) were added phenylisothiocyanate (0.25 g, 1.85 mmol) in acetone (5 ml) and sodium hydrogen carbonate (0.30 g). After the mixture was refluxed for 10 h, phenyisothiocyanate (0.50 g, 3.70 mmol) was added to the mixture, and then the mixture was refluxed for 2 h. The mixture was evaporated under reduced pressure to a residue, which was chromatographed and recrystallized to afford N-phenyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea (0.115 g, 16% yield) as crystalline material: mp 176.5°-177.0° C.

Workup

  1. temperatureAfter the mixture was refluxed for 10 h
  2. temperaturethe mixture was refluxed for 2 h
  3. customThe mixture was evaporated under reduced pressure to a residue, which
  4. customwas chromatographed
  5. customrecrystallized

Sources & evidence

ORD record
ord-b12814107bda4e7ba41dae78d4a3f659
Source dataset
uspto-grants-1990_04
Patent number
US04914112

Reaction notes

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