4-Nitrobenzaldehyde → HCID 178490058, compound

HRID 1817134Notes

Reaction equation

HRID 1817134 reaction equation
[CH3:1][O:2][C:3]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[C:44]([O:50][CH3:51])[C:4]=1[CH:5]=[CH:6][CH:7]([S:17]([CH:20]([CH:30]=[CH:31][C:32]1[C:37]([O:38][CH3:39])=[CH:36][C:35]([O:40][CH3:41])=[CH:34][C:33]=1[O:42][CH3:43])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([NH2:29])[CH:22]=1)(=[O:19])=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH2:16])[CH:9]=1.[N+:52]([C:55]1[CH:62]=[CH:61][C:58](C=O)=[CH:57][CH:56]=1)([O-:54])=[O:53]>CO.O>[CH3:51][O:50][C:44]1[CH:45]=[C:46]([O:48][CH3:49])[CH:47]=[C:3]([O:2][CH3:1])[C:4]=1[CH:5]=[CH:6][CH:7]([S:17]([CH:20]([CH:30]=[CH:31][C:32]1[C:33]([O:42][CH3:43])=[CH:34][C:35]([O:40][CH3:41])=[CH:36][C:37]=1[O:38][CH3:39])[C:21]1[CH2:22]/[C:23](=[N:29]\[C:58]2[CH:57]=[CH:56][C:55]([N+:52]([O-:54])=[O:53])=[CH:62][CH:61]=2)/[C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:19])=[O:18])[C:8]1[CH2:9]/[C:10](=[N:16]\[C:58]2[CH:61]=[CH:62][C:55]([N+:52]([O-:54])=[O:53])=[CH:56][CH:57]=2)/[C:11]([O:14][CH3:15])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 66912535HCID 66912535, compound

Product 1

HCID 178490058HCID 178490058, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,4,6-trimethoxystyryl-3-amino-4-methoxybenzylsulfone (10 mmol) in methanol (40 mL) is added 4-nitrobenzaldehyde (10 mmol). The solution is refluxed with vigorous stirring for 5 h. The reaction mixture is cooled, diluted with water and the aqueous mixture is then extracted twice with dichloromethane and organic layer is dried over anhydrous magnesium sulfate. The dried organic solution is evaporated and the residue is recrystallized to give (E)-2,4,6-trimethoxystyryl-3-(4-nitrophenylimino)-4-methoxybenzylsulfone.

Workup

  1. temperatureThe solution is refluxed
  2. temperatureThe reaction mixture is cooled
  3. extractionthe aqueous mixture is then extracted twice with dichloromethane and organic layer
  4. dry with materialis dried over anhydrous magnesium sulfate
  5. customThe dried organic solution is evaporated
  6. customthe residue is recrystallized

Sources & evidence

ORD record
ord-1e67f3bac93b4b0b982329d0a4c9e65c
Source dataset
uspto-grants-2009_10
Patent number
US07598232B2

Reaction notes

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