3,5-Dichloro-1-methylpyrazole-4-carbonyl chloride → 2-{2-Tert-butyloxazol-4-yl}-3-(3,5-dichloro-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile

HRID 1822638Notes

Reaction equation

HRID 1822638 reaction equation
CC(C)([O-])C.[K+].[C:7]([C:11]1[O:12][CH:13]=[C:14]([CH2:16][C:17]#[N:18])[N:15]=1)([CH3:10])([CH3:9])[CH3:8].[Cl:19][C:20]1[C:24]([C:25](Cl)=[O:26])=[C:23]([Cl:28])[N:22]([CH3:29])[N:21]=1>C1COCC1>[C:7]([C:11]1[O:12][CH:13]=[C:14]([C:16](=[C:25]([C:24]2[C:20]([Cl:19])=[N:21][N:22]([CH3:29])[C:23]=2[Cl:28])[OH:26])[C:17]#[N:18])[N:15]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 221694993,5-Dichloro-1-methylpyrazole-4-carbonyl chlorideHCID 221695172-(2-tert-Butyl-1,3-oxazol-4-yl)acetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 572553782-{2-Tert-butyloxazol-4-yl}-3-(3,5-dichloro-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrileYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.87 g of potassium tert-butoxide was suspended in 20 ml of THF, and a solution of 2.00 g of 2-tert-butyl-4-cyanomethyloxazole and 2.37 g of 3,5-dichloro-1-methylpyrazole-4-carbonyl chloride as dissolved in 10 ml of THF was dropwise added thereto with cooling with ice, and then stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After the resulting product was dried with anhydrous sodium sulfate, the solvent was evaporated out under reduced pressure. The residual product was purified through column chromatography (silica gel; n-hexane:ethyl acetate=4:1) to obtain 3.26 g of the intended compound.

Workup

  1. additionwas dropwise added
  2. temperaturewith cooling with ice
  3. extractionextracted with ethyl acetate
  4. washwashed with a small amount of water
  5. dry with materialAfter the resulting product was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated out under reduced pressure
  7. customThe residual product was purified through column chromatography (silica gel; n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c3939d34dc024717b585c814e57cdacd
Source dataset
uspto-grants-2006_05
Patent number
US07037880B2

Reaction notes

Loading…