Sodium Azide → HCID 178438077, compound

HRID 1824871Notes

Reaction equation

HRID 1824871 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, compoundYield 56.6%

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) and then nitrile (5c) (133 mg, 0.38 mmol). The mixture was stirred 10 min and heated to reflux. After refluxing 5 h, the mixture was diluted with 1N HCl and extracted with EtOAc. The combined organic layers were washed with water and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 10–20% methanol/CH2Cl2) to give tetrazole (5d) 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. temperatureheated to reflux
  2. temperatureAfter refluxing 5 h
  3. extractionextracted 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 chromatographed (silica gel, 10–20% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-4f51bcbd434a4953a47a529a1acb8c41
Source dataset
uspto-grants-2006_05
Patent number
US07045540B2

Reaction notes

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