Diphenyl N-Cyanocarbonimidate → HCID 178433151, compound

HRID 1378435Notes

Reaction equation

HRID 1378435 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[N:3]=1.[CH:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](OC2C=CC=CC=2)=[N:18][C:19]#[N:20])=[CH:12][CH:11]=1>COCCOC>[NH2:1][C:2]1[N:3]=[C:4]([CH3:9])[C:5]([NH:8][C:17](=[N:18][C:19]#[N:20])[O:16][C:13]2[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 27344216-methylpyridine-2,5-diamine

Product 1

HCID 178433151HCID 178433151, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of the product from Step 1 (4.34 g, 0.0353 mol), diphenylcyanocarbonimidate (8.4 g, 0.0353 mol) and ethylene glycol dimethyl ether (40 ml) was kept under nitrogen at ambient temperature (25° C.) for 18 hours. The mixture was concentrated and the residue was purified by silica gel chromatography and crystallization from MeOH-EtOAc-hexane to give 3.89 g of the titled product, mp 189°-190° C.

Workup

  1. customwas kept under nitrogen at ambient temperature
  2. custom(25° C.)
  3. customfor 18 hours
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by silica gel chromatography and crystallization from MeOH-EtOAc-hexane

Sources & evidence

ORD record
ord-d61b44f9c9094277bf0a0359d9dc68b2
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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