Hydrochloric Acid → 2-amino-3-bromo-5-chloro-N-(1-cyclopropylethyl)benzamide
Reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([NH:6][CH:7]([CH:9]1[CH2:11][CH2:10]1)[CH3:8])=[O:5].[H-].[Na+].[Br:19]Br.Cl>CN(C)C=O>[NH2:1][C:2]1[C:15]([Br:19])=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([NH:6][CH:7]([CH:9]1[CH2:11][CH2:10]1)[CH3:8])=[O:5]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
0.1 g of 2-amino-5-chloro-N-(1-cyclopropylethyl)benzamide was dissolved in 3 ml of N,N-dimethylformamide and cooled to 0° C. 0.02 g of sodium hydride was added, followed by stirring for one hour, and 0.09 g of bromine was added, followed by stirring for 2 hours. The reaction liquid was added to a 1 M-HCl aqueous solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/1) to obtain 0.08 g of the pale yellow desired produce (melting point: 177° C.).
Workup
- stirringby stirring for 2 hours
- customThe reaction liquid
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/1)
- customto obtain 0.08 g of the pale
- customyellow desired produce (melting point: 177° C.)
Sources & evidence
- ORD record
- ord-0a0ec19efa3148e4b8d1e758e586ac3d
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08115006B2
Reaction notes
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