Pyridine → 4-(1,1-Dimethylethyl)benzene-1,2-dicarbonitrile
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:14]([NH2:16])=O)[C:8](=[CH:12][CH:13]=1)[C:9]([NH2:11])=O)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>O>[C:1]([C:5]1[CH:6]=[C:7]([C:14]#[N:16])[C:8](=[CH:12][CH:13]=1)[C:9]#[N:11])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-t-butylphthalonitrile was prepared by fitting a 500 milliliter three-necked flask with a nitrogen inlet, a 100 milliliter pressure equalizing funnel, and a stopper, placing the flask in an ice bath, and charging the flask with 60 grams (0.2713 mole) of 4-t-butylphthalamide and 400 milliliters of pyridine. The resulting mixture was kept under a constant flow of nitrogen. Phosphorus oxychloride (49.7 milliliters, 0.5426 mole) was placed in the dropping funnel and added slowly to the pyridine solution to keep the temperature at about 4° C. The reaction was magnetically stirred for 4 hours and the mixture was then poured into a beaker containing 200 milliliters of crushed ice. Water was added until the total volume was 1,600 milliliters and a light brown solid was produced. The solid was removed by suction filtration, resulting in 31.24 grams (0.1696 mole) of 4-t-butylphthalonitrile, which exhibited a melting point of 58° to 59° C. The identity of the 4-t-butylphthalonitrile product was confirmed by IR spectrum.
Workup
- custom4-t-butylphthalonitrile was prepared
- customat about 4° C
- additionthe mixture was then poured into a beaker
- customa light brown solid was produced
- customThe solid was removed by suction filtration
Sources & evidence
- ORD record
- ord-6114a09f979d4247851c587faf2da7d0
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04916470
Reaction notes
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