Chlorosuccinimide → HCID 58542508, compound

HRID 1843084Notes

Reaction equation

HRID 1843084 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([O:11][CH:12]([F:14])[F:13])[CH:6]=1)=[O:4].[Cl:15]N1C(=O)CCC1=O>CN(C)C=O>[Cl:15][C:6]1[C:7]([O:11][CH:12]([F:14])[F:13])=[N:8][N:9]([CH3:10])[C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 58542532HCID 58542532, compound

Product 1

HCID 58542508HCID 58542508, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 400 mg (1.94 mmol) of methyl-3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate in 10 ml of N,N-dimethylformamide is admixed at 0° C. with 389 mg (2.91 mmol) of N-chlorosuccinimide and then stirred for 8 hours at 80° C. The reaction solution is poured onto water and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. This gives 466 mg of methyl 4-chloro-3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate (99%).

Workup

  1. additionThe reaction solution is poured onto water
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-d5a6af86baa5406bbb7de90afd8a2764
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

Loading…