Triethylamine → 3-Methyl-n-(1-methylethyl)-2-[(1-oxo-2-propenyl)amino]benzamide
Reaction equation
[NH2:1][C:2]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH:7]([CH3:9])[CH3:8])=[O:5].C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24].CN(C1C=CC=CN=1)C>ClCCl.Cl>[CH3:14][C:13]1[C:2]([NH:1][C:22](=[O:25])[CH:23]=[CH2:24])=[C:3]([CH:10]=[CH:11][CH:12]=1)[C:4]([NH:6][CH:7]([CH3:9])[CH3:8])=[O:5]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the title compound of Step B (0.93 g, 4.8 mmol) in dichloromethane (10 mL) was added triethylamine (0.876 mL, 6.2 mmol) and the mixture was cooled to 0° C. Acryloyl chloride (0.433 mL, 5.3 mmol) was then added and the mixture was warmed to ambient temperature and stirred overnight. Dimethylaminopyridine (1.0 g, 7.7 mmol) was then added followed by acryloyl chloride (0.475 mL, 5.8 mmol). The mixture was stirred at ambient temperature for 0.5 h before being diluted with 1N HCl and extracted twice with dichloromethane. The organic extracts were dried (MgSO4) and concentrated to give the product of Step C (0.62 g) as a white solid.
Workup
- temperaturethe mixture was warmed to ambient temperature
- stirringThe mixture was stirred at ambient temperature for 0.5 h
- extractionextracted twice with dichloromethane
- dry with materialThe organic extracts were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a657f347ef0e49a29c12131dbb390714
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087598B2
Reaction notes
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