Dimethylformamide → 1-(4-Fluorophenyl)-2-[phenyl(propan-2-yl)amino]ethan-1-one
Reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:14].CN(C)C=O>O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]([CH2:12][N:4]([CH:1]([CH3:3])[CH3:2])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:14])=[CH:16][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
562.9 g. (4.08 moles) of N-isopropylaniline is rapidly added to a solution of the crude product of Step 1 in 500 ml. of dimethylformamide stirred at 50° C. under nitrogen. The reaction mixture is stirred at 100° C. under nitrogen for 10 hours and allowed to cool to room temperature overnight. The reaction mixture is heated to 60° C., 2 l of water is added, and the mixture is cooled to 10° C. The obtained solids are collected, washed twice with 500 ml. portions of water and dissolved in 550 ml. of 95% ethanol at 75° C. The solution is cooled to 0° C., and the obtained solids are collected, washed three times with 100 ml. portions of 95% ethanol and vacuum dried at 35°-40° C. for 4 hours to obtain the 95.3% pure yellow product (466 g. (80.2% (two steps))), m.p. 78°- 81° C.
Workup
- temperatureto cool to room temperature overnight
- temperatureThe reaction mixture is heated to 60° C.
- temperaturethe mixture is cooled to 10° C
- customThe obtained solids are collected
- washwashed twice with 500 ml
- dissolutionportions of water and dissolved in 550 ml
- customat 75° C
- temperatureThe solution is cooled to 0° C.
- customthe obtained solids are collected
- washwashed three times with 100 ml
- dry with materialportions of 95% ethanol and vacuum dried at 35°-40° C. for 4 hours
Sources & evidence
- ORD record
- ord-6bd01cd2b12b4462a0e0eede11e20c82
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05354772
Reaction notes
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