Water → 1-Methoxycarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole

HRID 1586368Notes

Reaction equation

HRID 1586368 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:10]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[N:11][NH:12][CH:13]=1.Cl[C:23]([O:25][CH3:26])=[O:24].O>CN(C)C1C=CN=CC=1.C1COCC1>[CH3:26][O:25][C:23]([N:12]1[CH:13]=[C:9]([Cl:8])[C:10]([C:14]2[CH:15]=[C:16]([Cl:21])[CH:17]=[C:18]([Cl:20])[CH:19]=2)=[N:11]1)=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178478181HCID 178478181, compound

Product 1

HCID 218526441-Methoxycarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazoleYield 91.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2.52 g (0.0204 mol) of 4-dimethylaminopyridine and 18.3 ml (0.132 mol) of triethylamine are added to 30.55 g (0.12 mol) of 4-chloro-3-(3,5-dichlorophenyl)pyrazole dissolved in 300 ml of THF. A solution of 12.5 g (0.132 mol) of methyl chloroformate in 100 ml of THF is run, dropwise and at 0° C., into this solution. Stirring is continued for 20 h at room temperature. The reaction mixture is poured into 500 ml of water and extracted with ethyl acetate. After drying the organic phase and concentration under vacuum, the residue is triturated with 150 ml of heptane, filtered and dried. We obtain 33.5 g of 1-methoxycarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole, melting at 144° C.

Workup

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. customAfter drying
  4. concentrationthe organic phase and concentration under vacuum
  5. customthe residue is triturated with 150 ml of heptane
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-ceef507936c2482a9ec32ee7aa5c9d9e
Source dataset
uspto-grants-1999_08
Patent number
US05945382

Reaction notes

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