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 990737Notes

Reaction equation

HRID 990737 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-1eb6f02d17ff479a8c540fea753e5833
Source dataset
uspto-grants-2002_10
Patent number
US06462049B1

Reaction notes

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