Sodium Azide → HCID 18925215, compound

HRID 1289042Notes

Reaction equation

HRID 1289042 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[CH2:5][N:6]1[C:11]([C:12](=[O:21])[C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)=[C:10]([CH:22]([CH3:24])[CH3:23])[C:9](=[O:25])[NH:8][C:7]1=[O:26].[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C.CCOCC>[N:27]([CH2:2]/[CH:3]=[CH:4]/[CH2:5][N:6]1[C:11]([C:12](=[O:21])[C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)=[C:10]([CH:22]([CH3:24])[CH3:23])[C:9](=[O:25])[NH:8][C:7]1=[O:26])=[N+:28]=[N-:29]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 18925214HCID 18925214, compound

Product 1

HCID 18925215HCID 18925215, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 187 mg (0.5 mmol) of the compound obtained from Example 9 in 5 ml of DMF was added 98 mg (1.5 mmol) of sodium azide at room temperature. After 24 hours, the reaction mixture was diluted with ether, washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give a yellow oil, which was purified by flash chromatography using a mixture of ethyl acetate and hexane (1:2) as an eluent to afford 180 mg (yield 94%) of the title compound as a white solid.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under reduced pressure
  4. customto give a yellow oil, which
  5. customwas purified by flash chromatography
  6. additiona mixture of ethyl acetate and hexane (1:2) as an eluent

Sources & evidence

ORD record
ord-b60f5942a95c4f2f89c870f223ced9ed
Source dataset
uspto-grants-1998_05
Patent number
US05747500

Reaction notes

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