Diphenyl N-Cyanocarbonimidate → N-(5-Amino-6-chloro-3-pyridyl)-N'-cyano-O-phenylisourea

HRID 1378432Notes

Reaction equation

HRID 1378432 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([NH2:9])=[CH:4][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>[NH2:8][C:7]1[CH:6]=[C:5]([NH:9][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:4]=[N:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 221212822-Chloropyridine-3,5-diamine

Product 1

HCID 178512301N-(5-Amino-6-chloro-3-pyridyl)-N'-cyano-O-phenylisoureaYield 60.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of the product from Step 1 (1.80 g, 0.0125 mol) in ethylene glycol dimethyl ether (DME, 50 ml) was treated with diphenylcyanocarbonimidate (3.0 g, 0.0126 mol) and kept under nitrogen at ambient temperature (25° C.) for 96 hours. The precipitate was collected by filtration, washed with DME and dried to give 2.16 g of the titled product, mp 219°-220° C.

Workup

  1. customkept under nitrogen at ambient temperature
  2. custom(25° C.)
  3. customfor 96 hours
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with DME
  6. customdried

Sources & evidence

ORD record
ord-53095d2fc189461cabcd0bf533ae3c7c
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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