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

HRID 1586366Notes

Reaction equation

HRID 1586366 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[Cl:7][C:8]1[C:9]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)=[N:10][NH:11][CH:12]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH:1]([NH:4][C:5]([N:11]1[CH:12]=[C:8]([Cl:7])[C:9]([C:13]2[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]([Cl:19])[CH:18]=2)=[N:10]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 178478181HCID 178478181, compound

Product 1

HCID 218526341-Isopropylaminocarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazoleYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.95 g (0.011 mol) of isopropyl isocyanate are added, dropwise and at 0° C., to a solution of 2.55 g (0.01 mol) of 4-chloro-3-(3,5-dichlorophenyl)-1H-pyrazole and 1.55 ml (0.011 mol) of triethylamine in 20 ml of anhydrous DMF. Stirring is continued for 2 h at room temperature. The reaction mixture is poured into 100 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 2.10 g of 1-isopropylaminocarbonyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole, melting at 127° 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 50 ml of heptane
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-850f7cfbe8cf44ea8b8fe1a5760a2a29
Source dataset
uspto-grants-1999_08
Patent number
US05945382

Reaction notes

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