2-Amino-2-methyl-1-propanol → 2,4-dichloro-N-(1-hydroxy-2-methylpropan-2-yl)-6-methoxybenzamide
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[CH:4]=[O:5].BrN1C(=O)CCC1=O.[NH2:21][C:22]([CH3:26])([CH3:25])[CH2:23][OH:24]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[OH:24][CH2:23][C:22]([NH:21][C:4](=[O:5])[C:3]1[C:6]([O:11][CH3:12])=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Cl:1])([CH3:26])[CH3:25]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A suspension of 2,4-dichloro-6-methoxybenzaldehyde (3 g, 15 mmol) and N-bromosuccinimide (3.6 g, 20 mmol) in carbon tetrachloride (30 ml) was illuminated with a 150 W flood lamp under nitrogen with vigorous stirring on a steam bath for seven minutes. The cloudy mixture was cooled to 0° C., diluted with methylene chloride (30 ml) and treated dropwise with a solution of 2-amino-2-methylpropanol (3 ml, 30 mmol) in methylene chloride (30 ml). The ice bath was removed and the mixture was stirred at 20° C. for twenty hours.
Workup
- customwas illuminated with a 150 W flood lamp under nitrogen
- customThe ice bath was removed
- stirringthe mixture was stirred at 20° C. for twenty hours
Sources & evidence
- ORD record
- ord-b168dec584c0417883f9fb2e34f79f14
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04567289
Reaction notes
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