Benzyl Chloride → 2,2'-((Phenylmethyl)imino)bisethanol

HRID 1253369Notes

Reaction equation

HRID 1253369 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[OH:9][CH2:10][CH2:11][N:12]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:14][OH:15]

Participants

5

Reactant 3

HCID 7503Benzyl Chloride2×HCID 8113DiethanolamineHCID 10340Sodium Carbonate

Product 1

HCID 75532,2'-((Phenylmethyl)imino)bisethanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The process according to claim 2 which comprises adding one molar equivalent of benzyl chloride to a warmed mixture containing one molar equivalent of N,N-bis(2-hydroxyethyl)amine and 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; cooling the mixture to about 50° to 65° C.; filtering the mixture to remove inorganics; washing the filter-cake with toluene; drving the combined filtrate and washings by azeotropic distillation to produce a dry toluene solution containing a substantially quantitative yield of N,N-bis(2-hydroxyethyl)benzylamine.

Workup

  1. temperaturemaintaining the reaction temperature at about 70° to 100° C. for a short period
  2. temperaturecooling the mixture to about 50° to 65° C.
  3. filtrationfiltering the mixture
  4. customto remove inorganics
  5. washwashing the
  6. filtrationfilter-cake with toluene
  7. distillationby azeotropic distillation
  8. customto produce a dry toluene solution

Sources & evidence

ORD record
ord-feb5ad828bca4e60bf72b0cb04ac17e7
Source dataset
uspto-grants-1988_05
Patent number
US04748276

Reaction notes

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