Ammonia → HCID 67509984, compound

HRID 1770740Notes

Reaction equation

HRID 1770740 reaction equation
N[C:2](N)=[O:3].[NH2:5][C:6]([CH3:13])([CH3:12])[CH2:7][NH:8][CH2:9][CH2:10][OH:11].N>>[OH:11][CH2:10][CH2:9][N:8]1[CH2:7][C:6]([CH3:13])([CH3:12])[NH:5][C:2]1=[O:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1176UreaHCID 2268402-[(2-Amino-2-methylpropyl)amino]ethan-1-ol

Product 1

HCID 67509984HCID 67509984, compoundYield 41.7%

Procedure

A mixture of urea (5.4 g, 91 mmol) and 2-((2-amino-2-methylpropyl)amino)ethanol (12 g, 91 mmol) was heated in a 200° C. sand bath for approximately 45 min until ammonia evolution had ceased. The crude mixture was purified by column chromatography, eluting from silica gel with a gradient of 0-10% methanol in dichloromethane to give 6.0 g of a white solid. 1H NMR (CDCl3, 400 MHz) δ 1.33 (s, 6H), 3.21 (s, 2H), 3.27-3.30 (t, J=5.2, 2H), 3.69-3.71 (q, J=5.2 Hz, 2H), 4.01-4.04 (t, J=5.4, 1H), 5.31 (br s, 1H); LRMS (ESI/APCI) m/z 159 [M+H]+.

Workup

  1. customThe crude mixture was purified by column chromatography
  2. washeluting from silica gel with a gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-7f638c5f67d14ee7b7636c885850027d
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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