Sodium Hydroxide → 2,2,2-Trichloroethyl (3-tert-butyl-1-methyl-1H-pyrazol-5-yl)carbamate
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:11])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl[C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16]>C(OCC)(=O)C>[Cl:20][C:19]([Cl:22])([Cl:21])[CH2:18][O:17][C:15](=[O:16])[NH:11][C:7]1[N:8]([CH3:10])[N:9]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1Participants
5
Procedure
To a cooled (10° C.) solution of 5-tert-butyl-2-methyl-2H-pyrazol-3-ylamine (3.75 g, 24.5 mmol) and NaOH (1.5 g in 20 mL water) in ethyl acetate (45 mL) was added 2,2,2-trichloroethyl chloroformate (7.52 g, 35.5 mmol) over 5 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours. The mixture was diluted with ethyl acetate and the layers separated. The organic layer was washed with water, brine, dried over MgSO4, and concentrated under reduced pressure. The residue was diluted with ethyl acetate/dichloromethane and treated with aminomethyl silica (10 g) for 1 hour. The mixture was filtered and the filtrated concentrated under reduced pressure to provide the product.
Workup
- customthe layers separated
- washThe organic layer was washed with water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- additionThe residue was diluted with ethyl acetate/dichloromethane
- additiontreated with aminomethyl silica (10 g) for 1 hour
- filtrationThe mixture was filtered
- concentrationthe filtrated concentrated under reduced pressure
- customto provide the product
Sources & evidence
- ORD record
- ord-da1195a40714497e947cbe86c76fc19f
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799782B2
Reaction notes
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