Dimethylformamide → HCID 20201047, compound

HRID 978959Notes

Reaction equation

HRID 978959 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4](S(OCC)(=O)=O)=[CH:3][CH:2]=1.[CH3:14]N(C)C=O.O=[C:20]1[C:24]2[C:25]([C:29]3C=CC=CC=3)=[N:26][C:27](=[O:28])[C:23]=2[C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:21]1.[C:41](=[O:44])([O-])[O-].[K+].[K+]>CO>[O:28]=[C:27]1[C:23]2=[C:22]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:21]([CH2:20][CH3:24])[C:41](=[O:44])[C:14]2=[C:13]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:26]1[CH2:25][CH3:29]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6638Ethyl p-methylbenzenesulfonateHCID 11430Potassium CarbonateHCID 152175761,4-Dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole

Product 1

HCID 20201047HCID 20201047, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 16 parts of ethyl toluene-4-sulfonate in 15 parts of dimethylformamide is added to a mixture, warmed to 140°-142° C., of 5.8 parts of 1,4-diketo-3,6-diphenylpyrrolo-[3,4-c]-pyrrole, 12.2 parts of potassium carbonate and 60 parts of dimethylformamide in the course of 30 minutes, with stirring. The brown-yellow solution formed is subsequently stirred at 142° C. for 5 minutes, and 100 parts of methanol are added at 70° C. The yellow precipitate which has separated out is filtered off at 15° C., washed with methanol and with hot water at 90° C. and dried. The crude product (3.6 parts) is recrystallised first from 40 part of dimethylformamide and then from 100 parts of n-butanol. 2.8 parts of 1,4-diketo-2,5-diethyl-3,6-diphenylpyrrolo-[3,4-c]-pyrrole of the following formula are obtained in the form of orange-yellow needles of melting point 229°-230° C.: ##STR32##

Workup

  1. customThe brown-yellow solution formed
  2. stirringis subsequently stirred at 142° C. for 5 minutes
  3. customThe yellow precipitate which has separated out
  4. filtrationis filtered off at 15° C.
  5. washwashed with methanol and with hot water at 90° C.
  6. customdried
  7. customThe crude product (3.6 parts) is recrystallised first from 40 part of dimethylformamide

Sources & evidence

ORD record
ord-57a73f72232049e0ae771b14aa753baf
Source dataset
uspto-grants-1987_05
Patent number
US04666455

Reaction notes

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