Water → HCID 9796071, compound

HRID 1862569Notes

Reaction equation

HRID 1862569 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19]Br)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].[N-:21]=[N+:22]=[N-:23].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][N:21]=[N+:22]=[N-:23])[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 9883957HCID 9883957, compound

Product 1

HCID 9796071HCID 9796071, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 33 ml of dimethylformamide, was dissolved 1.1 g of the compound obtained in Example 5. To the resulting solution, was slowly added 325 mg of sodium azide. The obtained reaction solution was stirred at room temperature for 2 hours, and 80 ml of water and 120 ml of ethyl acetate were then added thereto to extract organic substances. The aqueous layer was extracted with 100 ml of ethyl acetate twice. The resulting extract was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford 925 mg (95%) of the title compound as a light-yellow oil.

Workup

  1. customThe obtained reaction solution
  2. extractionto extract organic substances
  3. extractionThe aqueous layer was extracted with 100 ml of ethyl acetate twice
  4. extractionThe resulting extract
  5. washwas washed with saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5963d55530784a52938d614ee0513d58
Source dataset
uspto-grants-2003_03
Patent number
US06538137B1

Reaction notes

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