Ammonium Chloride → HCID 178488700, compound

HRID 220758Notes

Reaction equation

HRID 220758 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:25])[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[O:12]2)=[C:7]([O:26][CH3:27])[CH:6]=1)#[N:2].[Cl-].[NH4+].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C=O)C>[NH:30]1[C:1]([CH2:3][O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9](=[O:25])[CH:10]=[C:11]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=4)[O:12]3)=[C:7]([O:26][CH3:27])[CH:6]=2)=[N:2][N:32]=[N:31]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59331779HCID 59331779, compound

Product 1

HCID 178488700HCID 178488700, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(cyanomethyloxy)-3′,4′,5-trimethoxy flavone (0.3 g, 0.82 mmol) obtained in Step 2, ammonium chloride (0.13 g, 2.45 mmol) and sodium azide (0.08 g, 1.23 mmol) were dissolved in N,N′-dimethylformamide (6 mL). After the reaction was carried out at 120° C. for 3 hours, the reaction solution was cooled to room temperature. The resulting solids were filtered and washed with ethyl acetate and n-hexane. The washed solids were dissolved in a 3:1 mixed solvent of chloroform and methanol and dried over anhydrous sodium sulfate to remove the solvent. The resulting residue was recrystallized from a 1:1 mixed solvent of ethyl acetate and chloroform to give 0.195 g (yield: 58%) of the title compound.

Workup

  1. filtrationThe resulting solids were filtered
  2. washwashed with ethyl acetate and n-hexane
  3. dissolutionThe washed solids were dissolved in a 3:1 mixed solvent of chloroform and methanol
  4. dry with materialdried over anhydrous sodium sulfate
  5. customto remove the solvent
  6. customThe resulting residue was recrystallized from a 1:1 mixed solvent of ethyl acetate and chloroform

Sources & evidence

ORD record
ord-939f60a68c62422b9e77a9ef5ae1112f
Source dataset
uspto-grants-2012_06
Patent number
US08203011B2

Reaction notes

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