Dimethylformamide → HCID 67425306, compound

HRID 220759Notes

Reaction equation

HRID 220759 reaction equation
C([P:4]([CH2:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:31])[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[O:18]2)=[C:13]([O:32][CH3:33])[CH:12]=1)([CH:6]([CH3:8])[CH3:7])=[O:5])(C)C.[N-]=[N+]=[N-].[Na+].CN(C)C=[O:41].C(OCC)(=O)C>O>[OH:5][P:4]([CH2:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:31])[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[O:18]2)=[C:13]([O:32][CH3:33])[CH:12]=1)([CH:6]([CH3:7])[CH3:8])=[O:41]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 67425485HCID 67425485, compound

Product 1

HCID 67425306HCID 67425306, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

7-{(diisopropylphosphoryl)-methyloxy}-3′,4′,5-trimethoxyflavone (0.5 g, 0.99 mmol, produced in Step 1 of Example 6) and sodium azide (0.5 g, 7.69 mmol) were added dropwise to N,N-dimethylformamide (20 mL) and warmed at 100° C. for 8 hours. The reaction solution was cooled to room temperature, and 50 mL of ethyl acetate and 50 mL of water were added dropwise, followed by separation of the organic layer from the aqueous layer. 10 mL of conc. hydrochloric acid was added dropwise to the aqueous layer which was then extracted with chloroform. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and then evaporated to afford 0.15 g (yield: 33%) of the title compound.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customfollowed by separation of the organic layer from the aqueous layer
  3. addition10 mL of conc. hydrochloric acid was added dropwise to the aqueous layer which
  4. extractionwas then extracted with chloroform
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8568ad180a354dee97e28224b35d4954
Source dataset
uspto-grants-2012_06
Patent number
US08203011B2

Reaction notes

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