Triethylamine → N-(2-bromopropionyl)-2-chloro-6-methylbenzylamine
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][NH2:5].C(N(CC)CC)C.[Br:18][CH:19]([CH3:23])[C:20](Br)=[O:21]>C(Cl)CCl>[Br:18][CH:19]([CH3:23])[C:20]([NH:5][CH2:4][C:3]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1])=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -35 °C
Procedure
A mixture of 35 parts of 2-chloro-6-methylbenzylamine and 30 parts of triethyl amine in 400 parts of ethylene chloride is stirred and cooled to -35°C. While keeping the temperature between -35° and -20° C., there is added dripwise a solution of 50 parts of 2-bromopropionyl bromide in 160 parts of ethylene chloride. Upon completion, the whole is stirred for one hour at room temperature. The reaction mixture is washed with diluted hydrochloric acid and once with water. The organic phase is dried over magnesium sulfate, filtered and evaporated. The solid residue is crystallized from a mixture of 400 parts of ethanol and 150 parts of water, yielding 40 parts of N-(2-bromopropionyl)-2-chloro-6-methylbenzylamine; mp. 168° -169° C.
Workup
- customthe temperature between -35° and -20° C., there
- stirringUpon completion, the whole is stirred for one hour at room temperature
- washThe reaction mixture is washed with diluted hydrochloric acid and once with water
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe solid residue is crystallized from a mixture of 400 parts of ethanol and 150 parts of water
Sources & evidence
- ORD record
- ord-1b6ce62300c14f95ac4f7a59af9136f3
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04017631
Reaction notes
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