Methyl 4-chloroacetoacetate → HCID 136046543, compound

HRID 1710758Notes

Reaction equation

HRID 1710758 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C(#N)CC>[CH3:18][O:17][C:15](=[O:16])[CH2:14][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=2)[O:7][CH:12]=1

Participants

4

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 650524-Hydroxybenzamide

Product 1

HCID 136046543HCID 136046543, compoundYield 411.2%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
98 °C

Procedure

A solution of 4-hydroxybenzamide (10 g, 7.3 mmol, 1 eq) and methyl 4-chloro-3-oxobutanoate (15 g, 11 mmol, 5 eq) in propionitrile (300 ml) is stirred at reflux (98° C.) during 3 days. After concentration under reduced pressure, the residue is purified over silicagel (eluent: dichloromethane/methanol/ammonia 90:9:1) to yield 7 g of methyl[2-(4-hydroxyphenyl)-1,3-oxazol-4-yl]acetate i50.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue is purified over silicagel (eluent: dichloromethane/methanol/ammonia 90:9:1)

Sources & evidence

ORD record
ord-0b9d5baf3ff3430cb33908f999102331
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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