2-Chloroethyl isocyanate → N-(2-Chloroethyl)-N'-[4-(4-hydroxybutyl)phenyl]urea

HRID 260768Notes

Reaction equation

HRID 260768 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[Cl:13][CH2:14][CH2:15][N:16]=[C:17]=[O:18]>>[Cl:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 150062264-(4-Aminophenyl)butan-1-OL

Product 1

HCID 15389130N-(2-Chloroethyl)-N'-[4-(4-hydroxybutyl)phenyl]ureaYield 55%

Procedure

To a solution of 4-(p-amino phenyl) butanol (2 g in 125 mL of ethyl ether) is added dropwise 1.25 g of 2-chloroethyl isocyanate. This solution is stirred for 3 h at room temperature, cooled at -20° C., and faltered. A white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated and recrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet): 3300 (NH), 1730 (C=O, ester), and 1640 cm-1 (C=O, ureido); 1H NMR (DMSO-d6): 8.65 (s, 1p, ArNH), 7.4-7.0 (dd, 4p, p-substituted Ar), 6.4 (broad t, 1p, NHCH2), 3.7-3.4 (m, 6p, ArCH2 and NHCH2CH2Cl), 2.85 (t, 2p, CH2OH), 2.3 (s, 1p, CH2OH), 1.85 (q, 2p, CH2CH2CH2), 1.45 (q, 2p, CH2CH2OH)

Workup

  1. temperaturecooled at -20° C.
  2. customA white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated
  3. customrecrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet)

Sources & evidence

ORD record
ord-722ee6e6b29e4f8491db458638d7e50e
Source dataset
uspto-grants-1996_06
Patent number
US05530026

Reaction notes

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