Ethanolamine → N-(2-hydroxyethyl)-N'-(2-benzyloxybenzyl)urea

HRID 980266Notes

Reaction equation

HRID 980266 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[CH2:11][N:12]=[C:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([CH2:21][NH2:22])[OH:20]>C(Cl)Cl>[OH:20][CH2:19][CH2:21][NH:22][C:13]([NH:12][CH2:11][C:10]1[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:14]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 137544342-Benzyloxybenzyl isocyanate

Product 1

HCID 13754437N-(2-hydroxyethyl)-N'-(2-benzyloxybenzyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 73.6 g of crude 2-benzyloxybenzyl isocyanate in 120 ml of methylene chloride is added dropwise in the course of 50 minutes to a solution of 36.8 ml of ethanolamine in 370 ml of methylene chloride. The reaction is slightly exothermic. After 2 hours the reaction solution is washed three times with 200 ml of water each time and dried using sodium sulphate. Methylene chloride is distilled off and the residue is recrystallised from isopropanol. The resulting product melts at 92°-94°.

Workup

  1. washAfter 2 hours the reaction solution is washed three times with 200 ml of water each time
  2. customdried
  3. distillationMethylene chloride is distilled off
  4. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-037fba8c5ed341f9abda27dc158ac253
Source dataset
uspto-grants-1987_01
Patent number
US04636511

Reaction notes

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