Sodium Azide → HCID 178488384, compound

HRID 650761Notes

Reaction equation

HRID 650761 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]([C:26]3[CH:31]=[CH:30][C:29]4[O:32][CH2:33][O:34][C:28]=4[CH:27]=3)[CH:18]2[C:35]#[N:36])=[CH:13][CH:12]=1.[Al](N=[N+]=[N-])(N=[N+]=[N-])N=[N+]=[N-]>C1COCC1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]([C:26]3[CH:31]=[CH:30][C:29]4[O:32][CH2:33][O:34][C:28]=4[CH:27]=3)[CH:18]2[C:35]2[NH:36][N:7]=[N:6][N:5]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 16708548HCID 16708548, compoundHCID 18703878HCID 18703878, compound

Product 1

HCID 178488384HCID 178488384, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To THF (2.5 ml) at −78° C. under an argon atmosphere was added aluminum chloride (90 mg, 0.67 mmol). After slowly warming to room temperature, sodium azide (130 mg, 2.2 mmol) was added, and the resulting mixture was heated at 70° C. for 5 min, then cooled to room temperature. To the reaction mixture was added a solution of (1RS, 2SR, 3SR)-1-(4-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carbonitrile (125 mg, 0.34 mmol) in THF (2.5 ml). After heating at 70° C. overnight, thin layer chromatographic analysis of the reaction mixture indicated the presence of starting material, so additional Al(N3)3 was prepared as above (1.34 mmol) in THF. To this was added the reaction mixture, and heating at 70° C. was resumed for an additional 5 h. The mixture was partitioned between EtOAc and 3M HCl. The aqueous phase was extracted with EtOAc, and the combined organic extracts were washed successively with H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo, and the residue was crystallized from EtOAc/hexanes to afford the title compound (78 mg, 56%). A portion of this material was further purified by MPLC (LiChroprep RP-18, MeOH/H2O=60/40) and then recrystallized; m.p. 155-157° C. (EtOAc/hexanes).

Workup

  1. temperaturethe resulting mixture was heated at 70° C. for 5 min
  2. temperaturecooled to room temperature
  3. temperatureAfter heating at 70° C. overnight
  4. additionTo this was added the reaction mixture
  5. temperatureheating at 70° C.
  6. customThe mixture was partitioned between EtOAc and 3M HCl
  7. extractionThe aqueous phase was extracted with EtOAc
  8. washthe combined organic extracts were washed successively with H2O and saturated aqueous NaCl
  9. customdried
  10. customThe solvent was removed in vacuo
  11. customthe residue was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-b04d3ff99934429da1404b6a1b1462f8
Source dataset
uspto-grants-2001_08
Patent number
US06274737B1

Reaction notes

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