Chlorosuccinimide → HCID 68326381, compound

HRID 2274006Notes

Reaction equation

HRID 2274006 reaction equation
[Cl:1][C:2]1([C:5]2[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH3:15])[N:6]=2)[CH2:4][CH2:3]1.[Cl:16]N1C(=O)CCC1=O>CN(C)C=O.O>[Cl:16][C:9]1[C:5]([C:2]2([Cl:1])[CH2:4][CH2:3]2)=[N:6][N:7]([CH3:15])[C:8]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 68326448HCID 68326448, compound

Product 1

HCID 68326381HCID 68326381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

500 mg (2.19 mmol) of ethyl 3-(1-chlorocyclopropyl)-1-methyl-1H-pyrazole-5-carboxylate are dissolved in 10 ml of N,N-dimethylformamide p.a., and 438 mg (3.28 mmol)) of N-chlorosuccinimide are added. The reaction mixture is heated at 80° C. for 15. The cooled reaction solution is diluted with water and extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and filtered. The solvent is removed under reduced pressure on a rotary evaporator. The crude product is filtered through silica gel and eluted with ethyl acetate. This gives 517 mg (80%) of ethyl 4-chloro-3-(1-chlorocyclopropyl)-1-methyl-1H-pyrazole-5-carboxylate in a purity of 89%.

Workup

  1. customThe cooled reaction solution
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure on a rotary evaporator
  7. filtrationThe crude product is filtered through silica gel
  8. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-bd0cbf348f214b45920a7ae327d41397
Source dataset
uspto-grants-2015_09
Patent number
US09126945B2

Reaction notes

Loading…