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Water → 2,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamate

HRID 353651
Notes
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Reaction equation

HRID 353651 reaction equation
Cl.[NH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:6]=[C:5]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=1.O.[OH-].[Na+].Cl[C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24]>CCOC(C)=O>[Cl:28][C:27]([Cl:30])([Cl:29])[CH2:26][O:25][C:23]([NH:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:6]=[C:5]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=1)=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 119912003-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine hydrochloride

Product 1

HCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
10 °C

Procedure

A mixture of 5-amino-3-t-butyl-1-p-tolylpyrazole hydrochloride (300 g, 1.13 mol), water (0.9 L), EtOAc (2.1 L) and NaOH (117 g, 2.84 mol) was stirred between 5-15° C. for 30 min. To this mixture, 2,2,2-trichloroethyl chloroformate (342 g, 1.58 mol) was added over 1 h between 5-15° C. The mixture was stirred at room temperature for 2 h, and then the aqueous layer was separated from the EtOAc layer. The EtOAc layer was washed with brine (2×0.9 L) and dried over MgSO4 (60 g). The EtOAc layer was collected by filtration. To this solution, heptane was added. A part of the solution was removed by distillation. The product was crystallized from the solution, collected by filtration and dried in vacuum oven to constant weight. Yield: 409 g, 90%. 1H NMR (CDCl3) δ 7.40 (d, 2H), 7.30 (d, 2H), 6.40 (s, 1H), 4.80 (s, 2H), 2.40 (s, 3H), 1.40 (s, 9H). MS (EI) m/z 404 (M+).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. customthe aqueous layer was separated from the EtOAc layer
  3. washThe EtOAc layer was washed with brine (2×0.9 L)
  4. dry with materialdried over MgSO4 (60 g)
  5. filtrationThe EtOAc layer was collected by filtration
  6. additionTo this solution, heptane was added
  7. customA part of the solution was removed by distillation
  8. customThe product was crystallized from the solution
  9. filtrationcollected by filtration
  10. customdried in vacuum oven to constant weight

Sources & evidence

ORD record
ord-1c777bdadd4e413ca7720b9c684bf8e4
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06753426B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes