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

HRID 1072872Notes

Reaction equation

HRID 1072872 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-facf0a28800c430b86754e762c7c575e
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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