Hydrochloric Acid → 4-(4-Chlorophenyl)-2-[(4-methylpyrimidin-2-yl)sulfanyl]-5-oxazolepropionic acid

HRID 350729Notes

Reaction equation

HRID 350729 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.Cl.[SH:20][C:21]1[N:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C)C=O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([S:20][C:21]3[N:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 118082582-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acidHCID 1784286872-Mercapto-4-methylpyrimidine hydrochloride

Product 1

HCID 865976574-(4-Chlorophenyl)-2-[(4-methylpyrimidin-2-yl)sulfanyl]-5-oxazolepropionic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixed solution of 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (1.43 g), 2-mercapto-4-methylpyrimidine hydrochloride (1.05 g), potassium carbonate (2.76 g) and N,N-dimethylformamide (20 mL) was stirred at 110° C. under a nitrogen atmosphere for 10 hrs. The reaction mixture was diluted with water, and acidified with 2N aqueous hydrochloric acid solution. The precipitated crystals were collected by filtration and recrystallized from methanol to give 3-[4-(4-chlorophenyl)-2-[(4-methylpyrimidin-2-yl)sulfanyl]-5-oxazolepropionic acid (1.65 g, yield 88%) as colorless prism crystals. melting point: 174–175° C.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7f8d35285c8048089b2f2539939c9430
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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