Water → [5-(2-fluoro-1-fluoromethyl-1-methyl-ethyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 729603Notes

Reaction equation

HRID 729603 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].C(=O)([O-])[O-].[Na+].[Na+].[F:16][CH2:17][C:18]([C:22]1[CH:23]=[C:24]([NH2:34])[N:25]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[N:26]=1)([CH2:20][F:21])[CH3:19].O>C1COCC1>[Cl:7][C:6]([Cl:9])([Cl:8])[CH2:5][O:4][C:2](=[O:3])[NH:34][C:24]1[N:25]([C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)[N:26]=[C:22]([C:18]([CH2:17][F:16])([CH3:19])[CH2:20][F:21])[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 685380205-(2-fluoro-1-fluoromethyl-1-methyl-ethyl)-2-p-tolyl-2H-pyrazol-3-ylamine

Product 1

HCID 68538054[5-(2-fluoro-1-fluoromethyl-1-methyl-ethyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2,2,2-trichloroethyl chloroformate (8.1 mmol, 1.1 mL) and aqueous sodium carbonate solution (4.8 mL) over a solution of 5-(2-fluoro-1-fluoromethyl-1-methyl-ethyl)-2-p-tolyl-2H-pyrazol-3-ylamine (7.3 mmol, 1.9 g) in 37 mL of THF. Stir for 24 hours. Pour the solution over water and extract in ethyl acetate. Combine organic layers and wash with saturated aq. sodium chloride. Dry over sodium sulfate, filter, and concentrate under reduced pressure to give [5-(2-fluoro-1-fluoromethyl-1-methyl-ethyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester. LCMS ES+ (m/z) 440 [M+H].

Workup

  1. extractionextract in ethyl acetate
  2. washCombine organic layers and wash with saturated aq. sodium chloride
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-2d68bfde4de44eaea10fea61ef90d66d
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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