Benzoyl chloride → HCID 20201043, compound

HRID 1381338Notes

Reaction equation

HRID 1381338 reaction equation
[O:1]=[C:2]1[C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:9](=[O:10])[C:5]=2[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:3]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[O:10]=[C:9]1[C:5]2=[C:4]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:3]([C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:2](=[O:1])[C:6]2=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]1[C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 152175761,4-Dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole

Product 1

HCID 20201043HCID 20201043, compound

Procedure

5.8 parts of 1,4-diketo-3,6-diphenylpyrrolo-[3,4-c]-pyrrole are stirred with 50 parts of benzoyl chloride at 190° C. for 22 hours. The starting material dissolves in the course of the reaction. On cooling of the reaction mixture, most of the reaction product precipitates. The reaction mixture is introduced into 320 parts of methanol, with stirring, and the mixture is stirred for 2 hours, without heating. The precipitated product is filtered off, washed with methanol and dried. 4.9 parts of ochre-coloured crude product which is purified by crystallisation from 50 parts of dimethylformamide, with addition of a filtration assistant, are obtained. 3.8 parts of 1,4-diketo-2,5-dibenzoyl-3,6-diphenylpyrrolo-[3,4-c]-pyrrole are obtained in the form of brownish-yellow crystals (formula XVIII). ##STR22##

Workup

  1. dissolutionThe starting material dissolves in the course of the reaction
  2. temperatureOn cooling of the reaction mixture, most of the reaction product
  3. customprecipitates
  4. additionThe reaction mixture is introduced into 320 parts of methanol
  5. stirringthe mixture is stirred for 2 hours
  6. temperaturewithout heating
  7. filtrationThe precipitated product is filtered off
  8. washwashed with methanol
  9. customdried
  10. filtration4.9 parts of ochre-coloured crude product which is purified by crystallisation from 50 parts of dimethylformamide, with addition of a filtration assistant
  11. customare obtained

Sources & evidence

ORD record
ord-7da7be67168c4525a34eb54cc26e0bdc
Source dataset
uspto-grants-1986_04
Patent number
US04585878

Reaction notes

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