Water → HCID 20407018, compound

HRID 615540Notes

Reaction equation

HRID 615540 reaction equation
Cl[CH2:2][CH2:3][CH:4]([CH3:17])[C:5]([NH:7][C:8]1[S:12][N:11]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:9]=1)=[O:6].[OH-].[K+].O>C(O)C.C(O)C.O>[CH3:14][C:13]([C:10]1[CH:9]=[C:8]([N:7]2[CH2:2][CH2:3][CH:4]([CH3:17])[C:5]2=[O:6])[S:12][N:11]=1)([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20407025HCID 20407025, compound

Product 1

HCID 20407018HCID 20407018, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of 0.5 g of 4-chloro-N-[3-(1,1-dimethylethyl)-5-isothiazolyl]-2-methylbutanamide dissolved in 30 ml ethanol was slowly added 0.112 g of potassium hydroxide dissolved in ethanol/water. The mixture was stirred at room temperature for about one-half hour and poured into water. The solution was extracted with diethyl ether, and the organic phase was washed with water, filtered, dried, filtered again, and finally evaporated to dryness under reduced pressure. The product crystallized from Skellysolve B to provide about 0.2 g of 1-[3-(1,1-dimethylethyl)-5-isothiazolyl]-3-methyl-2-pyrrolidinone. Yield 46%. mp 111°-113° C.

Workup

  1. extractionThe solution was extracted with diethyl ether
  2. washthe organic phase was washed with water
  3. filtrationfiltered
  4. customdried
  5. filtrationfiltered again
  6. customfinally evaporated to dryness under reduced pressure
  7. customThe product crystallized from Skellysolve B

Sources & evidence

ORD record
ord-52ac26effd334984b8e4393c5d6e2a16
Source dataset
uspto-grants-1985_02
Patent number
US04500343

Reaction notes

Loading…