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

HRID 615224
Notes
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Reaction equation

HRID 615224 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-877f5a95c7dd4568a1158bc422e4cb07
Source dataset
uspto-grants-1985_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04497813

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes