HCID 22061439, compound → HCID 23508587, compound

HRID 277320Notes

Reaction equation

HRID 277320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:15]3[C:14](=[O:16])[N:13]=[C:12]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)[C:11]=3[C:10](=[O:24])[N:9]=2)=[CH:4][CH:3]=1.[C:25]([O:33]C([O-])=O)([O:27][CH:28]([CH2:30][CH2:31][CH3:32])[CH3:29])=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:29][CH:28]([O:27][C:25]([N:13]1[C:12]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:11]2[C:15](=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]([C:25]([O:27][CH:28]([CH2:30][CH2:31][CH3:32])[CH3:29])=[O:33])[C:10]2=[O:24])[C:14]1=[O:16])=[O:33])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 2

HCID 22061439HCID 22061439, compoundHCID 131723137HCID 131723137, compound

Product 1

HCID 23508587HCID 23508587, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

4.28 g of 3,6-di-(4′-chlorophenyl)-pyrrolo[3,4,c]pyrrole-1,4-dione, 5.91 g 2-pentyl dicarbonate from Example B2, 0.40 g of 4-dimethylaminopyridine and 500 ml of dry tetrahydrofuran are mixed and the mixture is stirred at 55° C. for 4 hours. The suspension is filtered off with suction on a glass microfilter supporting a cotton filter, the solvent is evaporated off under reduced pressure, and the residue is admixed with 50 ml of isopropanol. After 30 minutes the precipitate is filtered off with suction and washed with 15 ml of isopropanol, and the yellow product is dried under reduced pressure to leave 2.86 g (41% of theory) of 2,5-di-2-pentyloxycarbonyl-3,6-di-(4′-chlorophenyl)-pyrrolo[3,4,c]pyrrole-1,4-dione as yellow powder. NMR (CDCl3) [ppm]: 67 =7.65 ppm (d,4H), 7.46 (d,4H), 4.98 (m,2H), 1.67-1.35 (m,8H), 1.26 (d,6H), 0.88 (t,6H).

Workup

  1. filtrationThe suspension is filtered off with suction on a glass microfilter
  2. filtrationfilter
  3. customthe solvent is evaporated off under reduced pressure
  4. filtrationAfter 30 minutes the precipitate is filtered off with suction
  5. washwashed with 15 ml of isopropanol
  6. customthe yellow product is dried under reduced pressure

Sources & evidence

ORD record
ord-e7cffa5f87174460aeaf7deb10c9596e
Source dataset
uspto-grants-2002_03
Patent number
US06355783B1

Reaction notes

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