Water → HCID 67548609, compound

HRID 2356721Notes

Reaction equation

HRID 2356721 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]([NH:12][CH:13]([C:20]([C:22]3[CH:26]=[C:25]([Cl:27])[S:24][CH:23]=3)=[O:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=O)[CH:8]=[CH:9][C:2]1=2.P(Cl)(Cl)(Cl)=O.O>CN(C)C=O>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]3[O:21][C:20]([C:22]4[CH:26]=[C:25]([Cl:27])[S:24][CH:23]=4)=[C:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=3)[CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 67547587HCID 67547587, compound

Product 1

HCID 67548609HCID 67548609, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the resulting crude product of ethyl 3-[(5-benzo[b]furoyl)amino]-4-(5-chlorothiophen-3-yl)-4-oxobutyrate (896 mg) in N,N-dimethylformamide (7 ml) was added phosphoryl chloride (0.48 ml) at room temperature, and the mixture was stirred at the same temperature overnight. To the reaction mixture was added water, the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane:acetone=7:1), and then, triturated with diethyl ether to obtain ethyl 2-(5-benzo[b]furyl)-5-(5-chloro-thiophen-3-yl)oxazol-4-ylacetate (349 mg) as colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (solvent: hexane:acetone=7:1)
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-1478d739be3444a78e123c3046180ba9
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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