4-(Dimethylamino)Benzaldehyde → (4E)-2-(1,3-benzothiazol-2-yl)-4-{[4-(dimethylamino)phenyl]-methylidene}-5-methyl-2,4-dihydro-3H-pyrazol-3-one

HRID 493010Notes

Reaction equation

HRID 493010 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[C:14](=[O:15])[CH2:13][C:12]([CH3:16])=[N:11]1.[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.N1CCCCC1>C(O)C.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[C:14](=[O:15])/[C:13](=[CH:23]/[C:22]2[CH:25]=[CH:26][C:19]([N:18]([CH3:27])[CH3:17])=[CH:20][CH:21]=2)/[C:12]([CH3:16])=[N:11]1

Participants

6

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 8082PiperidineHCID 459449Pyrazol-5(4H)-one, 1-(2-benzothiazolyl)-3-methyl-

Product 1

HCID 57679781(4E)-2-(1,3-benzothiazol-2-yl)-4-{[4-(dimethylamino)phenyl]-methylidene}-5-methyl-2,4-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1 g (4.32 mmol) of 2-(1,3-benzothiazol-2-yl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one and 1.93 g (12.96 mmol) of 4-(dimethylamino)benzaldehyde are stirred under reflux with the addition of 3 ml of piperidine in absolute ethanol for 2 hours. The mixture is then diluted with water and the bright red precipitate is filtered off, then washed with water and a small amount of cold methanol and dried under reduced pressure.

Workup

  1. filtrationthe bright red precipitate is filtered off
  2. washwashed with water
  3. dry with materiala small amount of cold methanol and dried under reduced pressure

Sources & evidence

ORD record
ord-97853ff632404409a3f0993a6fe48090
Source dataset
uspto-grants-2009_05
Patent number
US07534273B2

Reaction notes

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