Dimethylformamide → HCID 22930761, compound

HRID 1295257Notes

Reaction equation

HRID 1295257 reaction equation
Cl[C:2]1[O: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[O: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 22930735HCID 22930735, compound

Product 1

HCID 22930761HCID 22930761, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-(2-chloro-4-phenyl-5-oxazolyl)propionate (500 mg), 4-hydroxythiophenol (475 mg), potassium carbonate (520 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 2 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-oxazolyl]propionate as colorless crystals (637 mg, yield 95%). The crystals were recrystallized from toluene-hexane. melting point: 157–158° 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. concentrationconcentrated

Sources & evidence

ORD record
ord-e53921ad9d604789b41edcee52b063d4
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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