Methyl Isocyanate → N'-[4(1-dimethylaminomethyl-ethenyl)phenyl]-N-methyl urea

HRID 1379975Notes

Reaction equation

HRID 1379975 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)=[CH2:6])[CH3:3].[CH3:14][N:15]=[C:16]=[O:17].C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC>C(OCC)C>[CH3:1][N:2]([CH2:4][C:5]([C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:16](=[O:17])[NH:15][CH3:14])=[CH:9][CH:8]=1)=[CH2:6])[CH3:3]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9798523Di-n-butyl diacetoxy tinHCID 13187366HCID 13187366, compound

Product 1

HCID 13187360N'-[4(1-dimethylaminomethyl-ethenyl)phenyl]-N-methyl urea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 9.3 g (0.053 Mol) 4(1-dimethylaminomethyl-ethenyl)-aniline in 220 ml absolute diethylether are added 5 ml (0.085 Mol) methylisocyanate and the reaction solution, after addition of 0.3 ml dibutyl tin diacetate, stirred over night, at room temperature. The crystals that precipitated after 18 hours are filtered off and washed with petrol ether to give the analytically pure title compound, m.p. 123°-124°.

Workup

  1. customThe crystals that precipitated after 18 hours
  2. filtrationare filtered off
  3. washwashed with petrol ether

Sources & evidence

ORD record
ord-6d0354c9dfd14e968ff1f067752c05f3
Source dataset
uspto-grants-1986_04
Patent number
US04579585

Reaction notes

Loading…