Methyl Isocyanate → N-(6-chloro-3-pyridyl)-N-ethyl-N'-methylurea

HRID 1457907Notes

Reaction equation

HRID 1457907 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH3:10])=[CH:4][N:3]=1.[CH3:11][N:12]=[C:13]=[O:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([N:8]([CH2:9][CH3:10])[C:13]([NH:12][CH3:11])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 224503772-Chloro-N-ethylpyridin-5-amine

Product 1

HCID 22450505N-(6-chloro-3-pyridyl)-N-ethyl-N'-methylureaYield 93.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 30 ml of toluene was dissolved 2.4 g (0.015 mole) of 2-chloro-5-ethylaminopyridine, followed by addition of 3.4 g of methyl isocyanate. The mixture was refluxed for 15 hours. After cooling, the resulting crystals were collected by filtration, washed with a small amount of Et2O and dried. The procedure gave 3.0 g of N-(6-chloro-3-pyridyl)-N-ethyl-N'-methylurea as pale yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 15 hours
  2. temperatureAfter cooling
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with a small amount of Et2O
  5. customdried

Sources & evidence

ORD record
ord-fd246a12a33e423c95356369e1f2de68
Source dataset
uspto-grants-1998_12
Patent number
US05849768

Reaction notes

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