Sodium Azide → HCID 178438077, compound

HRID 584585Notes

Reaction equation

HRID 584585 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[C:9]1([C:15]2[CH2:21][CH2:20][CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16]=2[C:26]2[CH:31]=[CH:30][C:29]([CH:32]=[CH:33][C:34]#[N:35])=[CH:28][CH:27]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.Cl>[C:9]1([C:15]2[CH2:21][CH2:20][CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16]=2[C:26]2[CH:27]=[CH:28][C:29]([CH:32]=[CH:33][C:34]3[NH:35][N:7]=[N:6][N:5]=3)=[CH:30][CH:31]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 72346357HCID 72346357, compound

Product 1

HCID 178438077HCID 178438077, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of aluminum chloride (175 mg, 1.31 mmol) in THF (4 mL) at 0° C. was added sodium azide (170 mg, 2.61 mmol) then nitrile (5c) (133 mg, 0.38 mmol). The mixture was stirred 10 min and was heated to reflux. After refluxing 5 h the mixture was diluted with 1N HCl, and was extracted with EtOAc. The combined organic layers were washed with water and dried (MgSO4). The solvent was removed under reduced pressure and the residue was chromatographed (silica gel, 10-20% methanol/CH2Cl2) to give the tetrazole (5d, compound XIX, R3=H, R6=H as a white solid (84 mg, 56%): 1H NMR (CDCl3) δ 7.49 (d, J=16.8 Hz, 1H),7.34-7.06 (m, 12H), 6.91 (d, J=8.0 Hz, 2H), 6.79 (dd, J=7.3, 1.5 Hz, 1H), 2.84 (t, J=7.0 Hz, 2H), 2.38 (t, J=7.0 Hz, 2H), 2.16 (m, 2H); ESI m/z: 389 (M−H−, 100%).

Workup

  1. temperaturewas heated to reflux
  2. temperatureAfter refluxing 5 h the mixture
  3. extractionwas extracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was chromatographed (silica gel, 10-20% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-6a39a99c475d48b5943fa18ca05e20af
Source dataset
uspto-grants-2005_08
Patent number
US06927224B2

Reaction notes

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