2,2-Diethoxyethylamine → {2-[3-(2,2-Diethoxy-ethyl)-ureido]-ethyl}-carbamic acid tert-butyl ester

HRID 561025Notes

Reaction equation

HRID 561025 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].[C:10]([O:14][C:15](=[O:22])[NH:16][CH2:17][CH2:18][N:19]=[C:20]=[O:21])([CH3:13])([CH3:12])[CH3:11]>C1(C)C=CC=CC=1>[C:10]([O:14][C:15](=[O:22])[NH:16][CH2:17][CH2:18][NH:19][C:20]([NH:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])=[O:21])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 28343265tert-Butyl (2-isocyanatoethyl)carbamate

Product 1

HCID 86640494{2-[3-(2,2-Diethoxy-ethyl)-ureido]-ethyl}-carbamic acid tert-butyl esterYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add 2,2-diethoxy ethanamine (3.33 g, 25.04 mmol) to a solution of (2-isocyanato-ethyl)-carbamic acid tert-butyl ester (3.73 g, 20.03 mmol) in toluene (50 mL). After 1 hour, concentrate the mixture to afford a white solid (6.39 g). 1H NMR (DMSO-d6) δ 6.74 (t, J=5 Hz, 1H), 6.03 (t, J=5.6 Hz, 1H), 5.85 (t, J=5.8 Hz, 1H), 4.39 (t, J=5.4 Hz, 1H), 3.61-3.55 (m, 2H), 3.48-3.42 (m, 2H), 3.06 (t, J=5.7 Hz, 2H), 3.01 (q, J=6.2 Hz, 2H), 2.92 (q, J=6.2 Hz, 2H), 1.37 (s, 9H), 1.11 (t, J=6.4 Hz, 6H).

Workup

  1. concentrationconcentrate the mixture

Sources & evidence

ORD record
ord-daf64e12fada42c5889cc44293d3d1a9
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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