2-Bromothiazole → ethyl 2-[3-fluoro-4-(N-thiazol-2-ylamino)phenyl]propionate

HRID 1678875Notes

Reaction equation

HRID 1678875 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].Br[C:17]1[S:18][CH:19]=[CH:20][N:21]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[NH:8][C:17]1[S:18][CH:19]=[CH:20][N:21]=1

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 20364696Ethyl 2-(4-amino-3-fluorophenyl)propanoate

Product 1

HCID 20364701ethyl 2-[3-fluoro-4-(N-thiazol-2-ylamino)phenyl]propionateYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-(3-fluoro-4-aminophenyl)propionate (15 g) and 2-bromothiazole (11.7 g) is stirred at 150°-155° C for 15 minutes. The reaction mixture is dissolved in methylene chloride and the solution is washed with an aqueous solution of sodium hydrogen carbonate and dried. The solvent is evaporated. The residue is subjected to chromatography using alumina. From benzene eluate, ethyl 2-[3-fluoro-4-(N-thiazol-2-ylamino)phenyl]propionate (13.3 g) is obtained as oily substance boiling at 162°-164° C at 0.2 mmHg.

Workup

  1. washthe solution is washed with an aqueous solution of sodium hydrogen carbonate
  2. customdried
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-0e350db437c540e2907730dbbb7eeeb8
Source dataset
uspto-grants-1978_03
Patent number
US04077968

Reaction notes

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