Chloroform → 4-(1-(2-Fluoro-4-biphenyl)ethyl)-2-methylaminothiazole

HRID 1646578Notes

Reaction equation

HRID 1646578 reaction equation
Cl[CH2:2][C:3](=O)[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([F:18])[CH:7]=1)[CH3:5].C(Cl)(Cl)Cl.[CH3:24][NH:25][C:26]([NH2:28])=[S:27].C(=O)(O)[O-].[Na+]>CO.[Na+].[Cl-]>[CH3:24][NH:25][C:26]1[S:27][CH:2]=[C:3]([CH:4]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([F:18])[CH:7]=2)[CH3:5])[N:28]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 2723704MethylthioureaHCID 156760091-Chloro-3-(2-fluoro-4-biphenylyl)-2-butanone

Product 1

HCID 1242384-(1-(2-Fluoro-4-biphenyl)ethyl)-2-methylaminothiazoleYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

A mixture of (+)-1-chloro-3-(2-fluoro-4-biphenylyl)-2-butanone (27.7 mg, 0.1 mmol; [α]D25 ° C.+180° (c=0.744, CHCl3), N-methylthiourea (9 mg, 0.1 mmol) and sodium bicarbonate (9.2 mg, 0.11 mmol) in methanol (1 ml) was stirred at room temperature for 28 hr and the mixture was diluted with NaCl aq., then extracted with ethyl acetate. The extracts were dried with magnesium sulfate and evaporated under reduced pressure to a residue, which was chromatographed to afford (+)-2-methylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (21.9 mg, 70% yield): [α]D25 ° C.+10.7° (c=0.15, CHCl3); 70% ee.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts were dried with magnesium sulfate
  3. customevaporated under reduced pressure to a residue, which
  4. customwas chromatographed

Sources & evidence

ORD record
ord-c3a482f36bfe439fa489922deb1b1912
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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