Sodium Azide → HCID 22236947, compound

HRID 1743975Notes

Reaction equation

HRID 1743975 reaction equation
Cl[CH2:2][C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)[C:4]#[N:5].[N-:21]=[N+:22]=[N-:23].[Na+]>O>[N:21]([CH2:2][C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)[C:4]#[N:5])=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22236954HCID 22236954, compound

Product 1

HCID 22236947HCID 22236947, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 8.01 g of the compound obtained in Step 2 in 200 ml of dimethylformamide(DMF) was added 8.84 g of sodium azide. The resulting mixture was stirred for 18 hours at 140° C. After the reaction was completed, water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue thus obtained was purified by a silica gel column chromatography using a mixture of ethyl acetate and n-hexane of 1:6 to obtain 6.2 g of the title compound as an oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue thus obtained
  5. customwas purified by a silica gel column chromatography
  6. additiona mixture of ethyl acetate and n-hexane of 1:6

Sources & evidence

ORD record
ord-f97c1de322ee4aa6bbd1942c0c816a85
Source dataset
uspto-grants-2006_03
Patent number
US07012144B2

Reaction notes

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