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

HRID 974053Notes

Reaction equation

HRID 974053 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-12307d935f0c45ef83388485deaff5a4
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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