Hydrogen chloride-ethyl acetate → HCID 86644420, compound

HRID 2194734Notes

Reaction equation

HRID 2194734 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([S:15][C:16]2[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[N:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[N:11]=1)C)(C)(C)C.C(OCC)(=O)C.Cl>C(OCC)(=O)C.CO>[ClH:22].[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:12]1[C:13]([S:15][C:16]2[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[CH:14][C:10]([CH2:9][NH:7][CH3:6])=[N:11]1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86644421HCID 86644421, compound

Product 1

HCID 86644420HCID 86644420, compoundYield 166.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl({1-(2-chlorophenyl)-5-[(6-chloropyridin-3-yl)thio]-1H-pyrazol-3-yl}methyl)methylcarbamate (350 mg) was dissolved in ethyl acetate (3 mL) and methanol (2 mL), 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) was added and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from a mixed solvent of ethyl acetate and hexane, and recrystallized from a mixed solvent of ethyl acetate and ethanol to give the title compound as colorless crystals (yield 252 mg, 83%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from a mixed solvent of ethyl acetate and hexane
  3. customrecrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-485316bddf56462f835f97b6260cd87e
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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