Ethanolamine → HCID 13067040, compound

HRID 1759193Notes

Reaction equation

HRID 1759193 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[CH:4][N:3]=1.[CH2:21]([CH2:23][NH2:24])[OH:22].[OH-].[NH4+].ClC1N=CC=CN=1>CO.C(Cl)(Cl)Cl.O.C(O)C>[CH2:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:24][CH2:23][CH2:21][OH:22])[N:7]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

9

Reactant 4

HCID 700EthanolamineHCID 14923Ammonium HydroxideHCID 744042-ChloropyrimidineHCID 13067038HCID 13067038, compound

Product 1

HCID 13067040HCID 13067040, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2-chloro-4-(n-dodecylamino)pyrimidine (6.0 g, 0.02 m), ethanolamine (12.2 g, 0.2 m), ethanol (70 ml) and water (20 ml) is stirred and refluxed until thin-layer chromatography (silica gel; 10 parts chloroform, 0.2 parts methanol, 0.5 parts concentrated ammonium hydroxide) indicates the absence of the 2-chloropyrimidine compound. The ethanol is removed in vacuo, the residue is distributed between water and methylene chloride, the aqueous layer is extracted again with methylene chloride, the combined organic layer is washed well with water, dried (Na2SO4) and concentrated to leave a residue of 6.3 g (98%) of 4-(n-dodecylamino)-2-(2-hydroxyethylamino)pyrimidine as an oil which crystallizes readily on standing.

Workup

  1. customThe ethanol is removed in vacuo
  2. extractionthe aqueous layer is extracted again with methylene chloride
  3. washthe combined organic layer is washed well with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61057f6435254111af6ce56ba68991de
Source dataset
uspto-grants-1982_07
Patent number
US04339453

Reaction notes

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