Dimethylamine → HCID 22267613, compound

HRID 2298025Notes

Reaction equation

HRID 2298025 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[C:13]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=3[Cl:19])[N:7]=[CH:6][C:5]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:3][CH2:2]1.[CH3:25][NH:26][CH3:27]>C(Cl)Cl>[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[C:13]([S:15]([N:26]([CH3:27])[CH3:25])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=3[Cl:19])[N:7]=[CH:6][C:5]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 22267925HCID 22267925, compound

Product 1

HCID 22267613HCID 22267613, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 5-cyclopropyl-1-(2-chloro-5-{chlorosulfonyl}phenyl)-1H-pyrazole-4-carboxylate (0.315 g, 0.812 mmol) in CH2Cl2 (3 mL) was treated at 23° C. with dimethylamine (2 M in THF, 3 mL, 6 mmol). The resulting mixture was stirred for 15 min and concentrated in vacuo. The residue was partitioned between EtOAc and HCl (0.1 M aq). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Flash 40S™ chromatography (65:35 hexanes-EtOAc) to afford 0.276 g (86% yield) of desired product as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and HCl (0.1 M aq)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Flash 40S™ chromatography (65:35 hexanes-EtOAc)

Sources & evidence

ORD record
ord-0dc0e2859b2d404ebb3b907729439ab6
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Reaction notes

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