Sodium Azide → HCID 178450091, compound

HRID 427742Notes

Reaction equation

HRID 427742 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([CH3:24])=[CH2:23])=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].C([NH+](CC)CC)C>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([CH3:24])=[CH2:23])=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:27][N:26]=[N:25][N:18]=2)=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 18357763HCID 18357763, compound

Product 1

HCID 178450091HCID 178450091, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2-[N-(5-Bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]-5-cyanopyridine (reference example 8) (0.45 g, 1.16 mmol) in N-methylpyrrolidone (12 ml) was treated with sodium azide (228 mg, 3.5 mmol) followed by triethylammonium chloride (251 mg, 1.8 mmol) and heated with stirring at 120° C. (oil bath) for 7 hours under an argon balloon. The resultant red solution was poured into ice/water (30 ml), acidified and extracted twice with ethyl acetate (total 50 ml). The combined organic extracts were washed twice with water, dried (MgSO4) and evaporated to give a brown gum. The gum was purified by MPLC to give the title compound as an off-white foam (150 mg, 30%).

Workup

  1. temperatureheated
  2. extractionextracted twice with ethyl acetate (total 50 ml)
  3. washThe combined organic extracts were washed twice with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a brown gum
  7. customThe gum was purified by MPLC

Sources & evidence

ORD record
ord-b5ddb41c3c554aa68af8cd553bae1356
Source dataset
uspto-grants-2001_11
Patent number
US06313148B1

Reaction notes

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