Sodium Azide → HCID 178438077, compound

HRID 2253452Notes

Reaction equation

HRID 2253452 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) 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-879937c6a68a451a9094e479eb952709
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Reaction notes

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