Chloroacetyl chloride → 2-Chloro-N-(2,6-diisopropylphenyl)acetamide
Reaction equation
C(N(CC)CC)C.[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[C:12]=1[NH2:20])([CH3:10])[CH3:9].[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Cl:21][CH2:22][C:23]([NH:20][C:12]1[C:11]([CH:8]([CH3:10])[CH3:9])=[CH:16][CH:15]=[CH:14][C:13]=1[CH:17]([CH3:19])[CH3:18])=[O:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
222 mL (1.59 mol) of triethylamine are added to a solution of 300 mL (1.59 mol) of 2,6-diisopropyl-phenylamine (Starting material 3) in 1 litre of dichloromethane. The reaction mixture is cooled to 0° C., and 127 mL (1.59 mol) of chloroacetyl chloride are then added dropwise. Once the addition is complete, the ice bath is removed and the medium is stirred for 20 minutes. It is then poured into water and extracted with dichloromethane. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated off. The residue is filtered through silica gel (eluent: dichloromethane). The filtrate is evaporated and then triturated in heptane. 2-Chloro-N-(2,6-diisopropyl-phenyl)acetamide is obtained in the form of a white solid.
Workup
- additionOnce the addition
- customthe ice bath is removed
- additionIt is then poured into water
- extractionextracted with dichloromethane
- washwashed with water
- dry with materialThey are dried over sodium sulfate
- customThe solvents are evaporated off
- filtrationThe residue is filtered through silica gel (eluent: dichloromethane)
- customThe filtrate is evaporated
- customtriturated in heptane
Sources & evidence
- ORD record
- ord-1cb41b6cef974f16a7ab6309e699e4e5
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420682B2
Reaction notes
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