Thiourea → 2-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

HRID 974034Notes

Reaction equation

HRID 974034 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Cl[CH2:6][C:7](=O)[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([F:22])[CH:11]=1)[CH3:9]>O.[OH-].[Na+]>[NH2:1][C:2]1[S:3][CH:6]=[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:12]([F:22])[CH:11]=2)[CH3:9])[N:4]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 156760091-Chloro-3-(2-fluoro-4-biphenylyl)-2-butanone

Product 1

HCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazoleYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To thiourea (1.77 g, 23.3 mmol) in water (50 ml) was added 1-chloro-3-(2-fluoro-4-biphenylyl)-2-butanone (5.25 g, 19.0 mmol). After addition, the mixture was heated for 3 hr, and the solution was cooled to room temperature, then added IN sodium hydroxide to pH 8. The mixture was extracted with chloroform and the chloroform extracts were washed with water, dried over, and evaporated under reduced pressure to a residue, which was chromatographed to afford 2-amino-4-[1-(2-fluoro-4-biphenylyl)ethyl] thiazole (4.12 g, 73% yield) as crystalline material: mp 167°-168° C.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was heated for 3 hr
  3. extractionThe mixture was extracted with chloroform
  4. washthe chloroform extracts were washed with water
  5. customdried over, and
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-79d7895c1c7541b1b2bdcad12ac4a003
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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