Sodium hydride → N,N'-bis(n-butoxycarbonyl)-1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole

HRID 52608Notes

Reaction equation

HRID 52608 reaction equation
[O:1]=[C:2]1[C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:9](=[O:10])[C:5]=2[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:3]1.[H-].[Na+].Cl[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27]>O1CCCC1>[CH2:29]([O:28][C:26]([N:8]1[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]2[C:5](=[C:4]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:3]([C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])[C:2]2=[O:1])[C:9]1=[O:10])=[O:27])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 61140Butyl chloroformateHCID 152175761,4-Dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole

Product 1

HCID 70191840N,N'-bis(n-butoxycarbonyl)-1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrroleYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.5 g (0.00175 mol) of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole in 17 ml of tetrahydrofuran are added, under argon, 0.28 g (0.007 mol) of solid sodium hydride. After stirring for 24 hours, 0.67 ml (0.007 mol) of n-butyl chloroformate are added and the suspension is stirred overnight. The mixture is filtered and the filtrate is concentrated under vacuum. The residue is taken up in water/diethyl ether, the organic phase is dried over MgSO4 and then concentrated under vacuum. The residue is taken up in n-hexane and the precipitated yellow powder is collected by filtration and washed with a minor amount of n-hexane, giving 0.62 g (73% of theory) of N,N'-bis(n-butoxycarbonyl)-1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole as a yellow fluorescent powder.

Workup

  1. additionare added, under argon
  2. stirringthe suspension is stirred overnight
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate is concentrated under vacuum
  5. dry with materialthe organic phase is dried over MgSO4
  6. concentrationconcentrated under vacuum
  7. filtrationthe precipitated yellow powder is collected by filtration
  8. washwashed with a minor amount of n-hexane

Sources & evidence

ORD record
ord-66129e337d344ed5a9426bc67e89e139
Source dataset
uspto-grants-1997_04
Patent number
US05616725

Reaction notes

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