Methanol → HCID 53942766, compound

HRID 1196081Notes

Reaction equation

HRID 1196081 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14].[O-:16][C:17]#[N:18].[K+].CO>Cl.O>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:17]([NH2:18])=[O:16]

Participants

6

Reactant 3

HCID 887MethanolHCID 11378442Potassium cyanateHCID 22055164HCID 22055164, compound

Product 1

HCID 53942766HCID 53942766, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of this amine (4.6 g) in dilute hydrochloric acid (40 ml) and concentrated hydrochloric acid (12 ml) was treated with potassium cyanate (7.0 g) in water (10 ml). The mixture was refluxed for 18 hours and the solvent removed leaving a white solid. To this methanol (10 ml) was added and the mixture filtered. The solvent was evaporated from the filtrate which was then chromatographed on a basic alumina column eluting with 10% methanol in chloroform, to give a yellow solid which was washed with ether to give N,N-dimethyl-N-(11-ureidoundecyl)amine as a white solid (1.2g).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customthe solvent removed
  3. customleaving a white solid
  4. filtrationthe mixture filtered
  5. customThe solvent was evaporated from the filtrate which
  6. customwas then chromatographed on a basic alumina column
  7. washeluting with 10% methanol in chloroform
  8. customto give a yellow solid which
  9. washwas washed with ether

Sources & evidence

ORD record
ord-243bd2db0e8947e4929348afffccc106
Source dataset
uspto-grants-1992_05
Patent number
US05112922

Reaction notes

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