Pyridine → HCID 21327097, compound

HRID 614854Notes

Reaction equation

HRID 614854 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7](O)=O)[C:4]2[O:10][C:11]3C(C(O)=O)=CC=C[C:12]=3[C:3]=2[CH:2]=1.CC1C=CC(S([NH2:30])(=O)=O)=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O>[C:42]([C:41]1[C:11]2[O:10][C:4]3[C:5]([C:7]#[N:30])=[CH:6][CH:1]=[CH:2][C:3]=3[C:12]=2[CH:38]=[CH:39][CH:40]=1)#[N:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3022Dibenzofuran-4,6-Dicarboxylic AcidHCID 6269P-ToluenesulfonamideHCID 24819Phosphorus pentachloride

Product 1

HCID 21327097HCID 21327097, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To a mixture of one equivalent of 4,6-dibenzofurandicarboxylic acid [H. Gilman and R. Young, J. Am. Chem. Soc. 57, 1121 (1935)] and 2.2 equivalents of p-toluenesulfonamide is added 4.5 equivalents of phosphorous pentachloride. When the initial reaction subsides the reaction mixture is heated to 200° C. and the solid residue remaining is cooled and treated with pyridine and water. The suspension is filtered, washed with water and suspended in dilute sodium hydroxide solution followed by filtration and washing with water to give 4,6-dicyanodibenzofuran which can be recrystallized from a dimethylformamide-water combination. In like manner 3,7-dicyanodibenzofuran is prepared from 3,7-dibenzofurandicarboxylic acid [H. Sugil and H. Shindo, J. Pharm. Soc. Japan 54, 829 (1934)].

Workup

  1. customWhen the initial reaction
  2. temperaturethe solid residue remaining is cooled
  3. filtrationThe suspension is filtered
  4. washwashed with water
  5. filtrationfollowed by filtration
  6. washwashing with water

Sources & evidence

ORD record
ord-463da9d5e793419f9cf65052e5c0e7fa
Source dataset
uspto-grants-1979_03
Patent number
US04146624

Reaction notes

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