Diphenyl N-Cyanocarbonimidate → N'-Cyano-N-(2-dimethylamino-3-pyridyl)-O-phenylisourea

HRID 1378436Notes

Reaction equation

HRID 1378436 reaction equation
[NH2:1][C:2]1[C:3]([N:8]([CH3:10])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:11]1[CH:16]=[CH:15][C:14]([O:17][C:18](OC2C=CC=CC=2)=[N:19][C:20]#[N:21])=[CH:13][CH:12]=1>COCCOC>[C:20]([N:19]=[C:18]([O:17][C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1)[NH:1][C:2]1[C:3]([N:8]([CH3:10])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1)#[N:21]

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 15656134N2,N2-Dimethyl-2,3-pyridinediamine

Product 1

HCID 178483039N'-Cyano-N-(2-dimethylamino-3-pyridyl)-O-phenylisourea

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

According to the procedure of Example 5, Step 3, 3-amino-2-dimethylaminopyridine (1.41 g, 0.0108 mol) was allowed to react with diphenylcyanocarbonimidate (2.45 g, 0.0108 mol) in ethylene glycol dimethyl ether (20 ml), under nitrogen for 18 hours. The reaction mixture was concentrated and the residue chromatographed on silica gel with mixtures of MeOH--CHCl3 containing from 0 to 5% MeOH. The product amounted to 3.23 g.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue chromatographed on silica gel with mixtures of MeOH

Sources & evidence

ORD record
ord-02f6dd59c30e4d0c8b5b9fdd1482c265
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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