4-Aminobenzonitrile → 4-(((2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile

HRID 1699892Notes

Reaction equation

HRID 1699892 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH2:15][C:13](=[O:14])[O:12]1.[CH:20]([O-])([O-])OCC>C(O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][CH:20]=[C:15]2[C:16](=[O:17])[O:18][C:11]([CH3:19])([CH3:10])[O:12][C:13]2=[O:14])=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 53630039Ethylorthoformate

Product 1

HCID 116947054-(((2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrileYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of p-aminobenzonitrile (2.00 g), Meldrum's acid (2.56 g), ethyl orthoformate (2.76 g) and ethanol (10 ml) was heated at 120° C. (bath temperature) to evaporate the ethanol. Ethyl acetate was added to the obtained orange solid. The solid was pulverized, collected by filtration and washed with ethyl acetate to give the object compound (3.28 g) as a white powder.

Workup

  1. customto evaporate the ethanol
  2. additionEthyl acetate was added to the obtained orange solid
  3. filtrationcollected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3d412e743780466e841877e60d7dc848
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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