Dimethylformamide → HCID 22930693, compound

HRID 1295259Notes

Reaction equation

HRID 1295259 reaction equation
Cl[C:2]1[S:3][C:4]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[OH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][C:2]2[S:3][C:4]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:6]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 22930788HCID 22930788, compound

Product 1

HCID 22930693HCID 22930693, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-(2-chloro-4-phenyl-5-thiazolyl)propionate (380 mg), 4-hydroxythiophenol (341 mg), potassium carbonate (373 mg) and N,N-dimethylformamide (7 ml) was stirred at room temperature for 5 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and-concentrated to give methyl 3-[2-(4-hydroxyphenylthio)-4-phenyl-5-thiazolyl]propionate (464 mg, yield 93%) as colorless crystals. The crystals were recrystallized from toluene-hexane. melting point: 153–155° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with dilute hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentration-concentrated

Sources & evidence

ORD record
ord-e56bd30aa40e4ccb94f0b0ab6fa9ba40
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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