Chloroform → HCID 117724773, compound

HRID 628547Notes

Reaction equation

HRID 628547 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([O:16][CH3:17])[N:13]([CH3:18])[N:12]=2)=[CH:7][C:6]=1[CH3:19])([CH3:3])[CH3:2].[Cl:20]N1C(=O)CCC1=O.C(Cl)(Cl)Cl>O>[Cl:20][C:15]1[C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([CH3:19])[CH:7]=2)=[N:12][N:13]([CH3:18])[C:14]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 117724720HCID 117724720, compound

Product 1

HCID 117724773HCID 117724773, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, a mixture of 3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1-methyl-1H-pyrazole (described in Reference Preparation example 110) 5.8 g, N-chlorosuccinimide 3.3 g and chloroform 70 ml was stirred for 14 hours. Thereto was added water 50 ml and the resulting mixture was extracted with chloroform. The organic layer was washed with water, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 4-Chloro-3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1-methyl-1H-pyrazole 5.6 g.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ad50445e215406daba2136d36cf83d7
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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