Benzyl Chloride → 2,2'-((Phenylmethyl)imino)bisethanol
Reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[OH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][OH:13].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[OH:7][CH2:8][CH2:9][N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][OH:13]Participants
Procedure
The improvements in the above process aspects of the invention which afford a substantially quantitative yield of N,N-bis(2-chloroethyl)benzylamine, are based in part on modifications which eliminate formation of by-products and in part on a reverse in the order of addition of reactants. One improvement is based on the use of a molar equivalent quantity of sodium carbonate in the reaction of bis(2-hydroxyethyl)amine with benzyl chloride to produce N,N-bis(2-hydroxyethyl)benzyl amine, thereby completely inhibiting formation of the by-products N,N-dibenzyl-N-(2-hydroxyethyl)amine and N-benzyl-N-(2-benzyloxyethyl)-N-(2-hydroxyethyl)amine, which are produced in relatively large quantities (about 16% and 20% respectively) in the absence of said sodium carbonate. Another improvement is based on the addition of N,N-bis(2-hydroxyethyl)benzylamine in toluene solution to slightly more than a two molar excess of thionyl chloride rather than the heretofore reverse addition of thionyl chloride to N,N-bis(2-hydroxyethyl)benzylamine, thereby completely eliminating the formation of N-benzylmorpholine. Another improvement is the azeotropic distillation of the toluene solution of N,N-bis(2-hydroxyethyl)benzylamine to remove the water formed by the reaction, thereby avoiding the use of excess thionyl chloride to ensure completion of reaction in the chlorination step.
Workup
- additionin part on a reverse in the order of addition of reactants
Sources & evidence
- ORD record
- ord-5dde9cb01c0b4aaf8256bdd01f944b17
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04748276
Reaction notes
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