1,1-Bis(methylthio)-2-nitroethylene → 6,7-Dimethoxy-4-[4-(1-methylthio-2-nitrovinyl)-1-piperazinyl]quinazoline

HRID 2230091Notes

Reaction equation

HRID 2230091 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[CH3:21][S:22][C:23](SC)=[CH:24][N+:25]([O-:27])=[O:26]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:16][CH2:17][N:18]([C:23]([S:22][CH3:21])=[CH:24][N+:25]([O-:27])=[O:26])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 27584846,7-Dimethoxy-4-piperazin-1-yl-quinazoline

Product 1

HCID 701549166,7-Dimethoxy-4-[4-(1-methylthio-2-nitrovinyl)-1-piperazinyl]quinazolineYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (30 mL) of 6,7-dimethoxy-4-(1-piperazinyl)quinazoline described in South African Patent 67 06512 (1968) (Compound (i); 6.00 g, 21.9 mmol), commercially available 1,1-bis(methylthio)-2-nitroethylene (4.27 g, 25.8 mol) was added, followed by stirring under heating at 50 C for 9 hours and then heating under reflux for 2.5 hours. After the reaction solution was allowed to stand for cooling, the solvent was evaporated and then the resulting residue was purified by silica gel column chromatography to give the target compound (2.65 g, 6.78 mmol).

Workup

  1. additionwas added
  2. temperatureunder heating at 50 C for 9 hours
  3. temperatureheating
  4. temperatureunder reflux for 2.5 hours
  5. temperaturefor cooling
  6. customthe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c7243d41e0e04818b8e965a8cc3dc163
Source dataset
uspto-grants-2002_07
Patent number
US06423716B1

Reaction notes

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