Water → HCID 21852672, compound

HRID 1586359Notes

Reaction equation

HRID 1586359 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:10]([C:14]2[C:22]3[O:21][C:20]([F:24])([F:23])[O:19][C:18]=3[CH:17]=[CH:16][CH:15]=2)=[N:11][NH:12][CH:13]=1.[C:25](Cl)(=[O:27])[CH3:26].O>CN(C)C1C=CN=CC=1.C1COCC1>[C:25]([N:12]1[CH:13]=[C:9]([Cl:8])[C:10]([C:14]2[C:22]3[O:21][C:20]([F:24])([F:23])[O:19][C:18]=3[CH:17]=[CH:16][CH:15]=2)=[N:11]1)(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178506007HCID 178506007, compound

Product 1

HCID 21852672HCID 21852672, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

0.25 g (0.005 mol) of 4-dimethylaminopyridine and 4.25 g (0.042 mol) of triethylamine are added to 11.0 g (0.046 mol) of 4-chloro,3-(2,2-difluorobenzo-1,3-dioxol-4-yl)-1H-pyrazole (prepared as described in patent PH 91-033) dissolved in 100 ml of THF. A solution of 3.6 g (0.046 mol) of acetyl chloride in 50 ml of THF is run dropwise and at 0° C. onto this solution. Stirring is continued for 3 h at room temperature. The reaction mixture is poured into 300 ml of water and extracted with ethyl acetate. After drying the organic phase and concentration under vacuum, the residue is triturated with 50 ml of heptane, filtered and dried. We obtain 12.8 g of 1-acetyl-4-chloro-3-(2,2-difluorobenzo-1,3-dioxol-4-yl)pyrazole melting at 131° C.

Workup

  1. customis run dropwise and at 0° C. onto this solution
  2. extractionextracted with ethyl acetate
  3. customAfter drying
  4. concentrationthe organic phase and concentration under vacuum
  5. customthe residue is triturated with 50 ml of heptane
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-2f90d14469a943efb25faf88f779e719
Source dataset
uspto-grants-1999_08
Patent number
US05945382

Reaction notes

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