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

HRID 1437386Notes

Reaction equation

HRID 1437386 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:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[O:12]1.[CH:20](OCC)(OCC)OCC>C(O)C>[CH3:10][C:11]1([CH3:19])[O:16][C:15](=[O:17])[C:14](=[CH:20][NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[C:13](=[O:18])[O:12]1

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformate

Product 1

HCID 116947054-(((2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-aminobenzonitrile (12.5 g, 0.106 mol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (Meldrum's acid) (18.3 g, 0.127 mol) and triethyl orthoformate (16 ml) in ethanol (100 ml) was refluxed for 3 hours. After cooling to room temperature the product was filtered, washed with cold ethanol and air dried to afford an off-white solid (27.9 g, 97%).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationwas filtered
  3. washwashed with cold ethanol and air
  4. customdried

Sources & evidence

ORD record
ord-8122e9e7639b434980ce75982294c38b
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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