2,2,2-Trichloroethyl chloroformate → bis(2,2,2-trichloroethyl) 4-bromo-1-methyl-1H-pyrazol-3-ylimidodicarbonate

HRID 1744110Notes

Reaction equation

HRID 1744110 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[CH:5][N:4]([CH3:8])[N:3]=1.Cl[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:7][C:6]1[C:2]([N:1]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])=[N:3][N:4]([CH3:8])[CH:5]=1

Participants

5

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 27352834-bromo-1-methyl-1H-pyrazol-3-amine

Product 1

HCID 86594567bis(2,2,2-trichloroethyl) 4-bromo-1-methyl-1H-pyrazol-3-ylimidodicarbonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-4-bromo-1-methylpyrazole (2.69 g, 15.28 mmol) and DMAP (6.16 g, 50.45 mmol) in CH2Cl2 (100 mL) at 0° C. under dry nitrogen was added 2,2,2-trichloroethyl chloroformate (4.7 mL, 33.62 mmol) dropwise. The reaction mixture was warmed to rt and stirred for 1 hour. The reaction was quenched with water and the product extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 25/75, then 3/7 and 1/1) to afford bis(2,2,2-trichloroethyl) 4-bromo-1-methyl-1H-pyrazol-3-ylimidodicarbonate.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe product extracted with EtOAc (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography over silica gel (EtOAc/Hex, 25/75

Sources & evidence

ORD record
ord-79670eadd80f4aa89aa7fd95f2dd4bc7
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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