4-Ethylphenyl isocyanate → 2-(3-(2-Chlorobenzyl)-1-(2-hydroxyethyl)ureido)ethyl 4-ethylphenylcarbamate

HRID 655978

Reaction equation

HRID 655978 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][OH:10].[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1)[CH3:20]>C1COCC1.CN(C1C=CN=CC=1)C>[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:29])[O:13][CH2:12][CH2:11][N:7]([CH2:8][CH2:9][OH:10])[C:6]([NH:5][CH2:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[Cl:1])=[O:14])=[CH:23][CH:22]=1)[CH3:20]

Participants

5

Reactant 2

HCID 900074-Ethylphenyl isocyanateHCID 597784573-(2-Chlorobenzyl)-1,1-bis(2-hydroxyethyl)urea

Product 1

HCID 597784112-(3-(2-Chlorobenzyl)-1-(2-hydroxyethyl)ureido)ethyl 4-ethylphenylcarbamateYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-chlorobenzyl)-1,1-bis(2-hydroxyethyl)urea (2.3 g, 8.46 mmol), in THF were added DMAP and 4-ethylphenylisocyanate (1.24 g, 8.46 mmol). The reaction mixture was stirred for 1 h and concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give 2-(3-(2-chlorobenzyl)-1-(2-hydroxyethyl)ureido)ethyl 4-ethylphenylcarbamate (1.7 g, 48%). LRMS (M+H+) m/z 420.1.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-017d90adc65f43a48ca315388baf0ff2
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Linked notes

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