Triethylamine → 2-Bromo-N-isopropyl-N-p-tolyl-acetamide
Reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CCN(CC)CC.[Br:19][CH2:20][C:21](Br)=[O:22]>C(Cl)Cl>[Br:19][CH2:20][C:21]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 6.07 g (40.7 mmol) Isopropyl-p-tolyl-amine, prepared as in Part A, and 4.12 g (40.7 mmol, 1 equiv) Et3N in 50 mL DCM is added 8.22 g (40.7 mmol, 1 equiv) Bromoacetyl bromide in 25 mL DCM dropwise over 30 minutes at 0° C. The reaction mixture is stirred 1 h at 0° C. followed by warming to ambient temperature and stirring 18 h. The reaction mixture is washed with 1N HCl (3×50 mL), dried (MgSO4), filtered through a pad of 20 g silica gel eluted with 400 mL DCM, and concentrated in vacuo to give 9.39 g (34.5 mmol) of 2-Bromo-N-isopropyl-N-p-tolyl-acetamide as an amber oil: 1H NMR (CDCl3, 300 MHz) δ7.25 (d, 2H, J=8.1), 7.09 (d, 2H, J=8.3), 4.96 (m, 1H), 3.55 (s, 2H), 2.42 (s, 3H), 1.07 (d, 6H, J=6.8); TLC Rf =0.23 (EtOAc/Hexanes, 1:9).
Workup
- temperatureby warming to ambient temperature
- stirringstirring 18 h
- washThe reaction mixture is washed with 1N HCl (3×50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered through a pad of 20 g silica gel
- washeluted with 400 mL DCM
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-529b7937bbeb4414b010be8f7b5c5177
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859007
Reaction notes
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