N-Benzylnormechlorethamine → 2,2'-((Phenylmethyl)imino)bisethanol
Reaction equation
ClCCN(CC1C=CC=CC=1)CCCl.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][OH:29]>>[OH:23][CH2:24][CH2:25][N:26]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:27][CH2:28][OH:29]Participants
Procedure
In the process for preparing N,N-bis(2-chloroethyl)benzylamine by first reacting benzyl chloride with N,N-bis(2-hydroxyethyl)amine to produce N,N-bis(2-hydroxyethyl)benzylamine and then reacting N,N-bis(2-hydroxyethyl)benzylamine with thionvl chloride to produce N,N-bis(2-chloroethyl)benzylamine, the improvements which comprise adding about one molar equivalent of benzyl chloride to a warmed mixture containing about one molar equivalent of N,N-bis(2-hydroxyethyl)amine and about one molar equivalent of sodium carbonate, the addition rate of benzyl chloride being so as to maintain the exothermic reaction temperature at about 70° to 100° C.; maintaining the reaction temperature at about 70° to 100° C. for a short period; adding toluene to the reaction mixture; separating and drying the toluene solution containing N,N-bis(2-hydroxyethyl)benzylamine; adding said dry toluene solution to more than two molar equivalents of thionyl chloride heated to about 65°-75° C., the rate of addition being so as to maintain the reaction temperature at about 65°-75° C.; treating the reaction mixture with aqueous alkali; and, separating the toluene solution containing a substantially quantitative yield of the N,N-bis(2-chloroethyl)benzylamine.
Sources & evidence
- ORD record
- ord-373f497a4aea4c5e840e560ecc535909
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04748276
Reaction notes
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