Sodium Azide → HCID 178440795, compound

HRID 1824869Notes

Reaction equation

HRID 1824869 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[C:9]1([C:15]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]=[CH:32][C:33]#[N:34])=[CH:27][CH:26]=2)=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH3:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.Cl>[C:9]1([C:15]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]=[CH:32][C:33]3[NH:34][N:7]=[N:6][N:5]=3)=[CH:27][CH:26]=2)=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH3:18])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 53640530HCID 53640530, compound

Product 1

HCID 178440795HCID 178440795, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of aluminum chloride (1.82 g, 13.5 mmol) in THF (20 mL) at 0° C. was added sodium azide (1.77 g, 27 mmol) and then nitrile (4b) (888 mg, 2.65 mmol). The mixture was stirred 10 min and heated to reflux. After refluxing overnight, the mixture was diluted with 1N HCl, and extracted with EtOAc. The combined organic layers were washed with water, brine and then dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 10–20% methanol/CH2Cl2) to give tetrazole (4c) as a white solid (700 mg, 70%): 1H NMR (CDCl3) δ 7.63 (d, J=16.5 Hz, 1H), 7.39–7.11 (m, 12H), 6.98 (d, J=16.5 Hz, 1H), 6.91 (d, J=8.4 Hz, 2H), 2.48 (q, J=7.3 Hz, 2H), 0.94 (t, J=7.3 Hz, 3H); ESI m/z: 377 (M−H−, 100%).

Workup

  1. temperatureheated to reflux
  2. temperatureAfter refluxing overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  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-06c1293a89c64bc483aa37b0dd59deba
Source dataset
uspto-grants-2006_05
Patent number
US07045540B2

Reaction notes

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