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

HRID 862373Notes

Reaction equation

HRID 862373 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:8]2=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][C:11](=[O:12])[C:7]2=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:5]1.Cl[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27]>O1CCCC1>[CH2:29]([O:28][C:26]([N:10]1[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:8]2[C:7](=[C:6]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:5]([C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])[C:4]2=[O:3])[C:11]1=[O:12])=[O:27])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 61140Butyl chloroformateHCID 178517438HCID 178517438, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.28 g (0.007 mol) of solid sodium hydride is added to a suspension of 0.5 g (0.00175 mol) of 1,4-diketo-2,5-dihydro-3,6-diphenyl-pyrrolo[3,4-c]pyrrole in 17 ml of tetrahydrofuran in an argon atmosphere. After the resulting mixture is stirred for 24 hours, 0.67 ml (0.007 mol) of n-butyl chloroformate is added thereto, and the resulting suspension is stirred overnight. The mixture is filtered, and the filtrate is concentrated under reduced pressure. The residue is taken into water/diethyl ether, and the organic phase is dried over MgSO4 and then concentrated under reduced pressure. The residue is taken into n-hexane, and the yellow powder precipitated is collected by filtration, washed with a small amount of n-hexane to give 0.62 g (73% of the theoretical value) of N,N'-bis(n-butoxycarbonyl)-1,4-diketo-2,5-dihydro-3,6-diphenyl-pyrrolo[3,4-c]pyrrole as a yellow fluorescent powder.

Workup

  1. stirringthe resulting suspension is stirred overnight
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dry with materialthe organic phase is dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customthe yellow powder precipitated
  7. filtrationis collected by filtration
  8. washwashed with a small amount of n-hexane

Sources & evidence

ORD record
ord-829fe1dd67404a64bec1fd2a4bbb256d
Source dataset
uspto-grants-1998_02
Patent number
US05718998

Reaction notes

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