Isopropylamine → 3-(2-Chloroethyl)-1-(propan-2-yl)urea

HRID 2278961Notes

Reaction equation

HRID 2278961 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[Cl:5][CH2:6][CH2:7][N:8]=[C:9]=[O:10]>CC#N>[Cl:5][CH2:6][CH2:7][NH:8][C:9]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:10]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 34855443-(2-Chloroethyl)-1-(propan-2-yl)ureaYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of isopropylamine (3.00 g, 50.8 mmol) in MeCN (30 mL) was treated with 2-chloroethylisocyanate (6.00 g, 56.9 mmol), stirred at RT for 1 h and the resulting solid collected via filtration to afford 1-(2-chloroethyl)-3-isopropylurea (6.12 g, 73%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 5.96 (t, J=5.9 Hz, 1 H), 5.87 (d, J=7.7 Hz, 1 H), 3.62 (m, 1 H), 3.53 (t, J=6.3 Hz, 2 H), 3.25 (m, 2 H), 0.99 (d, J=6.5 Hz, 6 H); MS (ESI) m/z: 165.1 (M+H+).

Workup

  1. filtrationthe resulting solid collected via filtration

Sources & evidence

ORD record
ord-dd7629133b544ff6b5e8200a26332fa5
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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