Tert-Butylamine → 1-Tert-butyl-3-(2-chloroethyl)urea

HRID 2278959Notes

Reaction equation

HRID 2278959 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11]>CC#N>[C:1]([NH:5][C:10]([NH:9][CH2:8][CH2:7][Cl:6])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 2941631-Tert-butyl-3-(2-chloroethyl)ureaYield 83.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of t-butylamine (6.00 g, 82 mmol) in MeCN (120 mL) was treated with 2-chloroethylisocyanate (9.00 g, 85 mmol), stirred at RT for 1 h, and the resulting solid was collected via filtration to afford 1-(tert-butyl)-3-(2-chloroethyl)urea (12.2 g, 83%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 5.89 (t, J=5.9 Hz, 1 H), 5.82 (s, 1 H), 3.53 (t, J=6.2 Hz, 2 H), 3.24 (q, J=6.1 Hz, 2 H), 1.19 (s, 9 H); MS (ESI) m/z: 179.1 (M+H+).

Workup

  1. filtrationthe resulting solid was collected via filtration

Sources & evidence

ORD record
ord-d87bf607dc5b4960b21bf227b8e8a753
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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