Toluene → HCID 20201053, compound

HRID 978958Notes

Reaction equation

HRID 978958 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8]N(C)C=O.[O:13]=[C:14]1[C:18]2[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:20][C:21](=[O:22])[C:17]=2[C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:15]1.[C:35](=[O:38])([O-])[O-:36].[Na+].[Na+].[C:41]1(C)C=CC=C[CH:42]=1>C(O)C.O>[O:22]=[C:21]1[C:17]2=[C:16]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:15]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:14](=[O:13])[C:18]2=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:20]1[CH2:8][C:35]([O:36][CH2:41][CH3:42])=[O:38]

Participants

8

Reactant 5

HCID 1140TolueneHCID 6228Dimethylformamide2×HCID 7751Ethyl chloroacetateHCID 10340Sodium CarbonateHCID 152175761,4-Dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole

Product 1

HCID 20201053HCID 20201053, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 9.8 parts of ethyl chloroacetate and 20 parts of dimethylformamide is added to a mixture, warmed to 145° C., of 5.8 parts of 1,4-diketo-3,6-diphenylpyrrolo-[3,4-c]-pyrrole, 8.5 parts of sodium carbonate and 60 parts of dimethylformamide in the course of 30 minutes. The brown-yellow solution formed is subsequently stirred at 140°-145° C. for 30 minutes, cooled and poured onto 1,000 parts of water of 15° C. After the mixture has been left to stand at 20° C. for one hour, the aqueous phase is poured off and the crude product is heated to the boiling point with 200 parts of ethanol. The suspension formed is filtered at 20° C. and the product is washed with ethanol and then with water of 90° C. and dried. 5.6 parts of a yellow product of melting point 204°-208° C. are obtained. Pure 1,4-diketo-2,5-di-(carboethoxymethyl)-3,6 -diphenylpyrrolo-[3,4-c]-pyrrole of the following formula of melting point 209°-210° C. and M+ 460 is obtained by crystallisation from toluene. ##STR27##

Workup

  1. additionis added to a mixture
  2. customThe brown-yellow solution formed
  3. temperaturecooled
  4. waitAfter the mixture has been left
  5. waitto stand at 20° C. for one hour
  6. additionthe aqueous phase is poured off
  7. customThe suspension formed
  8. filtrationis filtered at 20° C.
  9. washthe product is washed with ethanol
  10. dry with materialwith water of 90° C. and dried
  11. custom5.6 parts of a yellow product of melting point 204°-208° C. are obtained

Sources & evidence

ORD record
ord-69cb8ce6becb48febf35eba1b00ddc58
Source dataset
uspto-grants-1987_05
Patent number
US04666455

Reaction notes

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