Ethanol → HCID 73669114, compound

HRID 2248304Notes

Reaction equation

HRID 2248304 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:3]=1.CS[C:15](SC)=[CH:16][N+:17]([O-:19])=[O:18].C(O)C>CO.ClCCl>[N+:17]([CH:16]=[C:15]1[NH:12][CH2:11][CH2:10][CH2:9][N:8]1[C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 702EthanolHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 19996035HCID 19996035, compound

Product 1

HCID 73669114HCID 73669114, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(6-chloro-3-pyridyl)-1,3-diaminopropane (6.0 g, 0.032 mol)(ex Example 2), 1,1-bis(methylthio)-2-nitroethene (5.34 g, 0.032 mol) and ethanol (100 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)hexahydropyrimidine as a pale yellow solid (3.1 g, 38%), m.p. 202° 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-8ad43b322518477fb8684a10d13a7ce2
Source dataset
uspto-grants-1991_08
Patent number
US05039686

Reaction notes

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