2-(Methylamino)ethanol → 3-(2-Chlorobenzyl)-1-(2-hydroxyethyl)-1-methylurea

HRID 655973

Reaction equation

HRID 655973 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[CH2:9][N:10]=[C:11]=[O:12]>C1COCC1>[Cl:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[CH2:9][NH:10][C:11](=[O:12])[N:2]([CH2:3][CH2:4][OH:5])[CH3:1]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 27333671-Chloro-2-(isocyanatomethyl)benzene

Product 1

HCID 597785693-(2-Chlorobenzyl)-1-(2-hydroxyethyl)-1-methylureaYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(methylamino)ethanol (600 mg, 7.99 mmol) in THF (5.0 mL) was added 2-chlorobenzylisocyanate (0.75 mL, 6.66 mmol). The reaction was stirred at rt for 30 min. The mixture was concentrated, re-dissolved in MeOH, filtered, and purified on RP-HPLC using a mixture of acetonitrile and H2O to give 3-(2-chlorobenzyl)-1-(2-hydroxyethyl)-1-methylurea (950 mg, 49%). LRMS (M+H+) m/z 243.0.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionre-dissolved in MeOH
  3. filtrationfiltered
  4. custompurified on RP-HPLC
  5. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-e6c3c01e7dfb42728e030745a6eddff6
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Linked notes

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