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

HRID 1646557Notes

Reaction equation

HRID 1646557 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 to 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 to 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-6e09f7650fce43d3a05c8f568b1914d3
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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