Dimethylformamide → HCID 22610642, compound

HRID 843493Notes

Reaction equation

HRID 843493 reaction equation
C[O-].[Na+].[N+:4]([C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([N+]([O-])=O)=[CH:14][CH:15]=3)[CH:10]([CH:23]3[O:27][CH2:26][CH2:25][O:24]3)[C:9]=2[CH:8]=1)([O-:6])=[O:5].CN(C)[CH:30]=[O:31]>O>[CH3:30][O:31][C:13]1[CH:14]=[CH:15][C:16]2[C:17]3[C:9](=[CH:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:19][CH:18]=3)[CH:10]([CH:23]3[O:24][CH2:25][CH2:26][O:27]3)[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 22610640HCID 22610640, compound

Product 1

HCID 22610642HCID 22610642, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

For a period of two hours, 8 parts of sodium methoxide was added to a solution of 10 parts of 2-(2,7-dinitro-9-fluorenyl)-1,3-dioxolane in 300 parts of dimethylformamide contained within a 5 liter flask at room temperature. The mixture was magnetically stirred for 20 hours. All of the mixture was then diluted with 1800 parts of water. A yellow solid was precipitated therefrom, collected on a filter, washed with water and dried under vacuum. The dried filtered product was further purified in a chromatography column packed with silica gel (Merck Grade 60) and developed by methylene chloride to provide 8.2 parts of product (86% yield).

Workup

  1. customcontained within a 5 liter flask at room temperature
  2. customA yellow solid was precipitated
  3. customcollected on a filter
  4. washwashed with water
  5. customdried under vacuum
  6. filtrationThe dried filtered product
  7. customwas further purified in a chromatography column

Sources & evidence

ORD record
ord-4cf2d357a0ab401f9e291de0467a9955
Source dataset
uspto-grants-2002_04
Patent number
US06379590B1

Reaction notes

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