Isopropanol → 4-(1-(2-Fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid

HRID 256771

Reaction equation

HRID 256771 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH3:9])=[N:5][C:4]=1[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:14]([F:24])[CH:13]=1)[CH3:11])=[O:2].CC(C)=[O:27].OS(O)(=O)=O.O=[Cr](=O)=O.[Cr](O)(O)(=O)=O.CC(O)C>CC(C)=O.S(=O)(=O)(O)O.O>[F:24][C:14]1[CH:13]=[C:12]([CH:10]([C:4]2[N:5]=[C:6]([NH:8][CH3:9])[S:7][C:3]=2[C:1]([OH:27])=[O:2])[CH3:11])[CH:17]=[CH:16][C:15]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 24425Chromic AcidHCID 19785543HCID 19785543, compoundHCID 131709961Jones' reagent2×

Product 1

HCID 197855604-(1-(2-Fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acidYield 20%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

5-Formyl-4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylaminothiazole (1.00 g, 2.9 mmoles) was dissolved in acetone (20 ml). Jones reagent (chromic acid (VI) dissolved in a mixture of concentrated sulfuric acid and water) (2 ml) was added dropwise thereinto while cooling the system with ice, after which it was stirred for one hour. Then, an additional 2 ml of Jones reagent was added dropwise and the resulting mixture was stirred for one hour. A small quantity of 2-propyl alcohol was added to the reaction mixture, it was extracted with ether, and the ether layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to obtain the desired 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid (205 mg, 0.58 mmole, yield 20%) as a white crystalline product.

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling the system with ice
  3. stirringthe resulting mixture was stirred for one hour
  4. extractionwas extracted with ether
  5. washthe ether layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9a21952cd5604db0878d4fd1b474390a
Source dataset
uspto-grants-1993_11
Patent number
US05258396

Linked notes

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