Ethanol → 2-Chloro-5-[2-(nitromethylidene)imidazolidin-1-yl]pyridine

HRID 2248305Notes

Reaction equation

HRID 2248305 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.CS[C:14](SC)=[CH:15][N+:16]([O-:18])=[O:17].C(O)C>CO.ClCCl>[N+:16]([CH:15]=[C:14]1[NH:11][CH2:10][CH2:9][N:8]1[C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 19996028HCID 19996028, compound

Product 1

HCID 713407752-Chloro-5-[2-(nitromethylidene)imidazolidin-1-yl]pyridineYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(6-chloro-3-pyridyl)-1,2-diaminoethane (0.7 g, 0.0041 mol)(ex Example 4), 1,1-bis(methylthio)-2-nitroethene (0.7 g, 0.0042 mol) and ethanol (25 ml) was heated under reflux for 24 hours. The resulting mixture was evaporated to leave a dark brown oil which was subjected to flash chromatography on a silica column using silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm), and with 2% w methanol in dichloromethane as eluent. The resulting product was recrystallized from ethanol to give 2-nitromethylene-1-(6-chloro-3-pyridyl)imidazolidine as a pale yellow solid (0.225 g, 25%), m.p. 201° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customThe resulting mixture was evaporated
  4. customto leave a dark brown oil which
  5. customThe resulting product was recrystallized from ethanol

Sources & evidence

ORD record
ord-cae6ddf35a564b59a0af092a57cd3f5d
Source dataset
uspto-grants-1991_08
Patent number
US05039686

Reaction notes

Loading…