4-(Dimethylamino)Benzaldehyde → 4-(2,3-Dihydro-1H-perimidin-2-yl)-N,N-dimethylaniline

HRID 2166806Notes

Reaction equation

HRID 2166806 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>C(O)C>[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]2[NH:12][C:10]3[C:11]4[C:6]([CH:7]=[CH:8][CH:9]=3)=[CH:5][CH:4]=[CH:3][C:2]=4[NH:1]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 680671,8-Diaminonaphthalene

Product 1

HCID 2566604-(2,3-Dihydro-1H-perimidin-2-yl)-N,N-dimethylanilineYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.2 g (0.02 mole) of 1,8-diaminonaphthalene and 3.0 g (0.02 mole) of p-dimethylaminobenzaldehyde in 35 ml of ethanol was refluxed for 2 hours. After cooling, the resulting precipitate was filtered and recrystallized from ethanol. There were obtained 3.8 g of 2-(p-dimethylaminophenyl)-2,3-dihydroperimidine as colorless crystals, m.p. 165°-166° C. (Compound No. 18).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was filtered
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b0735ae2d7f7448aae71e8feb3008010
Source dataset
uspto-grants-1983_06
Patent number
US04389321

Reaction notes

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