Methyl 4-chloroacetoacetate → HCID 59457469, compound

HRID 1710740Notes

Reaction equation

HRID 1710740 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Cl:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][CH:16]=1>C(#N)CC.ClCCl>[Cl:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]2[O:20][CH:2]=[C:3]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[N:21]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 144071764-(3-Chloropropoxy)benzamide

Product 1

HCID 59457469HCID 59457469, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7854PropionitrileSolvent

Procedure

Methyl 4-chloro-3-oxobutanoate (4.32 ml, 37.44 mmol, 2 eq) is added to a solution of 4-(3-chloropropoxy)benzamide (4 g, 18.72 mmol, 1 eq) in propionitrile (50 ml). The mixture is heated at reflux for 48 h. The mixture is then diluted with dichloromethane and filtered. The solvent is removed under vacuum and the residue is purified on silica gel (eluent: ethyl acetate) to give 2.8 g methyl {2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}acetate ax62 as a brown oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 48 h
  3. filtrationfiltered
  4. customThe solvent is removed under vacuum
  5. customthe residue is purified on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-eb81096c822f4c67bd7d046559e55f24
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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