HCID 22061439, compound → HCID 23508585, compound

HRID 277321Notes

Reaction equation

HRID 277321 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:35]C([O-])=O)([O:27][CH:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[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][CH2:32][CH2:33][CH3:34])[CH3:29])=[O:35])[C:10]2=[O:24])[C:14]1=[O:16])=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 2

HCID 22061439HCID 22061439, compoundHCID 131723138HCID 131723138, compound

Product 1

HCID 23508585HCID 23508585, compoundYield 45%

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, 7.26 g of 2-heptyl dicarbonate from Example B3, 0.20 g of 4-dimethylaminopyridine and 300 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 100 ml of isopropanol. After 30 minutes the precipitate is filtered off with suction, washed with isopropanol and dried under reduced pressure to leave 3.46 g (45% of theory) of 2,5-di-2-heptyloxycarbonyl-3,6-di-(4′-chlorophenyl)-pyrrolo[3,4,c]pyrrole-1,4-dione as orange crystals. NMR (CDCl3) [ppm]: δ=7.67 (d,4H), 7.45 (d,2H), 4.67 (q,2H), 1.53 (m,2H), 1.48 (m,2H), 1.28 (m,16H), 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 isopropanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-292edf8f31dc4ade8d2e5ea4b01aa87f
Source dataset
uspto-grants-2002_03
Patent number
US06355783B1

Reaction notes

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