Sodium Azide → HCID 178446927, compound

HRID 2210411Notes

Reaction equation

HRID 2210411 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH+:6]1C=CC=C[CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:17]=[CH:18][C:19]([NH:21][C:22]1[C:27]2[O:28][CH2:29][CH2:30][O:31][C:26]=2[CH:25]=[CH:24][CH:23]=1)=[O:20]>CN(C)C=O.Cl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:17]=[CH:18][C:19]([NH:21][C:22]1[C:27]2[O:28][CH:29]([C:7]3[NH:6][N:3]=[N:2][N:1]=3)[CH2:30][O:31][C:26]=2[CH:25]=[CH:24][CH:23]=1)=[O:20]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 69401Einecs 211-027-4HCID 53942416HCID 53942416, compound

Product 1

HCID 178446927HCID 178446927, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (490 mg) and pyridinium chloride (870 rag) were added to a solution of 8-(3-methoxy-4-pentyloxycinnamoyl) amino-1,4-benzodioxane (560 mg; synthesized in reference example 2) in dry dimethylformamide (3 ml). In an atmosphere of argon, the solution was stirred for 1.5 hrs at 100° C. The reaction solution cooled to room temperature was poured into IN hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried, and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (390 mg) having the following physical data:

Workup

  1. temperatureThe reaction solution cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a4aafc52ce644f2a9a0bb990fa0c9405
Source dataset
uspto-grants-1995_10
Patent number
US05459134

Reaction notes

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