HCID 22061439, compound → HCID 18314450, compound

HRID 277319Notes

Reaction equation

HRID 277319 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)[O:26][CH:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:30][CH2:29][CH2:28][CH:27]([O:26][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:26][CH:27]([CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH3:33])=[O:35])[C:10]2=[O:24])[C:14]1=[O:16])=[O:35])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 2

HCID 22061439HCID 22061439, compoundHCID 131723136HCID 131723136, compound

Product 1

HCID 18314450HCID 18314450, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.14 g of 3,6-di-(4′-chlorophenyl)-pyrrolo[3,4,c]pyrrole-1,4-dione (Pigment Red 254), 7.26 g of 4-heptyl pyrocarbonate from Example B1, 0.30 g of 4-dimethylaminopyridine and 150 ml of dry tetrahydrofuran are mixed and the mixture is stirred at room temperature for 165 minutes. The suspension is filtered through 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 16 hours the precipitate is filtered off with suction and dried under reduced pressure to leave 1.90 g (49% of theory) of 2,5-di-4-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), 7.46 (d,4H), 4.98 (m,2H), 1.55 (m,8H), 1.30 (m,8H), 0.90 (t,6H).

Workup

  1. filtrationThe suspension is filtered through a glass microfilter
  2. filtrationfilter
  3. customthe solvent is evaporated off under reduced pressure
  4. filtrationAfter 16 hours the precipitate is filtered off with suction
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-449a6b89fc8a437891c58f28a4990919
Source dataset
uspto-grants-2002_03
Patent number
US06355783B1

Reaction notes

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