Diethyl Ether → HCID 178512256, compound

HRID 865675Notes

Reaction equation

HRID 865675 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](OC2C=CC=CC=2)=[N:17][C:18]#[N:19])=[CH:11][CH:10]=1.CCOCC.CO.C(Cl)(Cl)Cl>C=C>[C:18]([N:17]=[C:16]([O:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)[NH:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[CH:4][CH:3]=1)#[N:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 793055-Amino-2-chloropyridineHCID 688090Diphenyl N-CyanocarbonimidateHCID 21584188Chloroform methanol

Product 1

HCID 178512256HCID 178512256, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6325EthyleneSolvent

Procedure

A stirred mixture of 5-amino-2-chloropyridine (1.3 g, 0.01 mol) and diphenylcyanocarbonimidate (2.4 g, 0.01 mol) in 15 ml of ethylene glycoldimethyl ether (DME), under nitrogen, was kept at 60° C. for 24 hours and at 85° C. for 6 hours when it was allowed to cool to room temperature. The solvent was removed in vacuo and the residue was heated to a melt at 120° C., under nitrogen, for 1 hour to complete the reaction as shown by TLC (5% MeOH/CHCl3). This was allowed to cool and was triturated with Et2O to give a solid that was collected by filtration. The solid was washed with Et2O to give 2.61 g of the titled product.

Workup

  1. customThe solvent was removed in vacuo
  2. temperaturethe residue was heated to a melt at 120° C., under nitrogen, for 1 hour
  3. customthe reaction
  4. temperatureto cool
  5. customwas triturated with Et2O
  6. customto give a solid
  7. filtrationthat was collected by filtration
  8. washThe solid was washed with Et2O

Sources & evidence

ORD record
ord-fe2c592282ad4818ae8d76cea7922209
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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