Potassium Carbonate → HCID 14097269, compound

HRID 568708Notes

Reaction equation

HRID 568708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([SH:17])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([O:26][C:27](=[O:32])[C:28](Br)([CH3:30])[CH3:29])[CH3:25]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([S:17][C:28]([CH3:30])([CH3:29])[C:27]([O:26][CH2:24][CH3:25])=[O:32])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 135589640HCID 135589640, compound

Product 1

HCID 14097269HCID 14097269, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.2 g of 3-(4-chlorophenyl)-6-mercapto-1,2-benzisoxazole, 2.52 g of potassium carbonate, 2.39 g of ethyl-2-bromo-2-methylpropionate and 75 ml dimethylformamide is heated at 60° C. for 8 hr. The reaction mixture is poured onto ice/dil hydrochloric acid and extracted with ether. The combined ether extracts are washed with dil sodium hydroxide solution, saturated sodium chloride solution and the solvent is removed in vacuo to afford a yellow oil. The oil is distilled in a Kugelrohr oven at 175° C. and 1.0 mm Hg to give an oil which crystallizes on standing. The solid is recrystallized from isopropyl ether using a brine-chilled Buchner funnel to afford ethyl 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]thio}-2-methylpropionate.

Workup

  1. additionThe reaction mixture is poured onto ice/dil hydrochloric acid
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with dil sodium hydroxide solution, saturated sodium chloride solution
  4. customthe solvent is removed in vacuo
  5. customto afford a yellow oil
  6. distillationThe oil is distilled in a Kugelrohr oven at 175° C.
  7. custom1.0 mm Hg to give an oil which
  8. customcrystallizes
  9. customThe solid is recrystallized from isopropyl ether using a brine-
  10. temperaturechilled Buchner funnel

Sources & evidence

ORD record
ord-1d3ee7de8f164a18bf37346cae539497
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

Loading…