p-Fluoronitrobenzene → 1,3-dimethyl-6-{4-[3-(4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

HRID 1729279Notes

Reaction equation

HRID 1729279 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:18])[N:4]([CH3:19])[C:3]1=[O:20].[N+:21]([C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][CH:25]=1)([O-:23])=[O:22]>CS(C)=O>[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:27]3[CH:28]=[CH:29][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:18])[N:4]([CH3:19])[C:3]1=[O:20]

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 190117511,3-dimethyl-6-[4-(3-aminopropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 190120931,3-dimethyl-6-{4-[3-(4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.50 g of the previously obtained compound h and 1.90 g of 4-nitrofluorobenzene were added to 20 ml of dimethyl sulfoxide, and the resultant mixture was then heated at 80° C. for 3 hours. After the mixture was allowed to stand for cooling, the precipitated crystals were collected by filtration, washed, and then dried to obtain 2.75 g of 1,3-dimethyl-6-[4-(3-[4-nitroanilino]-propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound g).

Workup

  1. temperaturefor cooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-f2fd503631b348cc821aafc6a2070682
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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