4-Chloro-2-methylbutanoyl chloride → HCID 20407025, compound

HRID 615539Notes

Reaction equation

HRID 615539 reaction equation
[CH3:1][C:2]([C:5]1[CH:9]=[C:8]([NH2:10])[S:7][N:6]=1)([CH3:4])[CH3:3].[CH3:11][CH:12]([CH2:16][CH2:17][Cl:18])[C:13](Cl)=[O:14]>C1(C)C=CC=CC=1>[Cl:18][CH2:17][CH2:16][CH:12]([CH3:11])[C:13]([NH:10][C:8]1[S:7][N:6]=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH:9]=1)=[O:14]

Participants

4

Reactant 2

HCID 137705824-Chloro-2-methylbutanoyl chlorideHCID 151170133-tert-Butyl-1,2-thiazol-5-amine

Product 1

HCID 20407025HCID 20407025, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2.4 g of 3-(1,1-dimethylethyl)-5-aminoisothiazole dissolved in 150 ml of toluene under nitrogen was added 2.3 g of 2-methyl-4-chlorobutyric acid chloride. The reaction mixture was refluxed for about 24 hours and cooled. The solvent was evaporated under reduced pressure, and the product was isolated from the residue by chromatography over silica gel eluting with an ethyl acetate/Skellysolve B solvent mixture. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford, following crystallization from toluene/Skellysolve B, 0.5 g of 4-chloro-N-[3-(1,1-dimethylethyl)-5-isothiazolyl]-2-methylbutanamide. Yield 12%. mp 144°-146° C.

Workup

  1. temperatureThe reaction mixture was refluxed for about 24 hours
  2. temperaturecooled
  3. customThe solvent was evaporated under reduced pressure
  4. customthe product was isolated from the residue by chromatography over silica gel eluting with an ethyl acetate/Skellysolve B solvent mixture
  5. additionFractions containing the major component
  6. customthe solvent was evaporated
  7. customto afford
  8. customcrystallization from toluene/Skellysolve B, 0.5 g of 4-chloro-N-[3-(1,1-dimethylethyl)-5-isothiazolyl]-2-methylbutanamide

Sources & evidence

ORD record
ord-14ad40eb1f5c42d68853b51b8b3743d4
Source dataset
uspto-grants-1985_02
Patent number
US04500343

Reaction notes

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