Dimethylcarbamoyl Chloride → N,N-Dimethyl-N'-(2-diisopropylaminoethyl)-N'-(4,6-dimethyl-2-pyrimidinyl)urea

HRID 2058157Notes

Reaction equation

HRID 2058157 reaction equation
[CH:1]([N:4]([CH:16]([CH3:18])[CH3:17])[CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24].[OH-].[Na+]>C(O)C.C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:26])[C:23]([N:7]([CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:16]([CH3:18])[CH3:17])[C:8]1[N:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[N:13]=1)=[O:24]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 233499002-(2-Diisopropylaminoethylamino)-4,6-dimethylpyrimidine

Product 1

HCID 23349935N,N-Dimethyl-N'-(2-diisopropylaminoethyl)-N'-(4,6-dimethyl-2-pyrimidinyl)urea

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-(2-diisopropylaminoethylamino)-4,6-dimethyl pyrimidine (17.0 g. 0.068 mole) and sodium hydride (50% in mineral oil) (4.19 g., 0.86 mole) in 175 ml. of dry toluene is stirred under nitrogen at 85°-95° C. for one half hour and then heated under reflux for one half hour. Dimethylcarbamoyl chloride (8.6 g., 0.08 mole) is added and heating under reflux is continued for twenty-four hours. The reaction is cooled and ethanol (10 ml) and sodium hydroxide (75 ml., 3.3 N) are added. The aqueous layer is extracted with methylene chloride and the extracts are dried over sodium sulfate and concentrated to an oil. The oil is distilled at 0.5 mm of Hg and the product boiling at 155°-158° C. is collected.

Workup

  1. temperatureheated
  2. temperatureunder reflux for one half hour
  3. temperatureheating
  4. temperatureunder reflux
  5. waitis continued for twenty-four hours
  6. temperatureThe reaction is cooled
  7. extractionThe aqueous layer is extracted with methylene chloride
  8. dry with materialthe extracts are dried over sodium sulfate
  9. concentrationconcentrated to an oil
  10. distillationThe oil is distilled at 0.5 mm of Hg
  11. customthe product boiling at 155°-158° C. is collected

Sources & evidence

ORD record
ord-04d66cbb2a3f4c918344fd331317f542
Source dataset
uspto-grants-1980_07
Patent number
US04215121

Reaction notes

Loading…