Potassium Carbonate → alpha-[(5-Acetylamino-4-chloro-2-methoxycarbonylphenyl)oxy]-gamma-butyrolactone

HRID 894611

Reaction equation

HRID 894611 reaction equation
[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:16])[CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:24]1[CH2:29][CH2:28][O:27][C:25]1=[O:26]>CN(C)C=O>[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:16][CH:24]2[CH2:29][CH2:28][O:27][C:25]2=[O:26])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 13329485Methyl 4-acetamido-5-chloro-2-hydroxybenzoate

Product 1

HCID 12925954alpha-[(5-Acetylamino-4-chloro-2-methoxycarbonylphenyl)oxy]-gamma-butyrolactone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

51 g. of Methyl 4-acetylamino-5-chloro-2-hydroxybenzoate and 36.8 g. of anhydrous potassium carbonate were suspended in 350 ml. of N,N-dimethylformamide. To the suspension was added 55 g. of α-bromo-γ-butyrolactone, and the mixture was stirred at 60° C. for 12 hours. The solvent was evaporated off under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to remove the solvent. The residue was dissolved in chloroform, and subjected to column chromatography on silica gel, using chloroform as the eluent. The product was recrystallized from methanol. By the above procedure there was obtained α-[(5-acetylamino-4-chloro-2-methoxycarbonylphenyl)oxy]-γ-butyrolactone as pale yellow prisms, m.p. 118°-119° C.

Workup

  1. additionTo the suspension was added 55 g
  2. customThe solvent was evaporated off under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customto remove the solvent
  9. dissolutionThe residue was dissolved in chloroform
  10. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-12974d29ce31466e91d9eb068bf367af
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Linked notes

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