Acetonitrile → 2-[6-(2-Chloro-4-methoxyphenoxy)hexyl]tetrazole

HRID 232098Notes

Reaction equation

HRID 232098 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]SC1SCC(=O)N=1.C(#N)C.[NH:27]1[CH:31]=[N:30][N:29]=[N:28]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:28]1[N:29]=[N:30][CH:31]=[N:27]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonate2×HCID 189218352-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-oneHCID 178418441HCID 178418441, compound2×

Product 1

HCID 189219092-[6-(2-Chloro-4-methoxyphenoxy)hexyl]tetrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Stir overnight at room temperature 300 mg. of the iodide prepared in Examples 2 and 3, 3 ml. acetonitrile, 63 mg. 1-H-tetrazole and 274 mg. cesium carbonate in a reaction flask. Add an additional. 189 mg. 1-H-tetrazole and 100 mg. cesium carbonate, let stir one week at room temperature. Work up the reaction mixture in methylene chloride with a water wash. Elute on a coarse silica column with methylene chloride then ethyl acetate/methylene chloride. Isolate two fractions of the title compound, the less polar fraction and the more polar fraction. One of the fractions is the 1-substituted tetrazole and the other fraction is the 2-substituted tetrazole.

Workup

  1. additionAdd an additional
  2. washwash
  3. washElute on a coarse silica column with methylene chloride

Sources & evidence

ORD record
ord-f91566f3fa834e319e6d04b3d0116695
Source dataset
uspto-grants-1989_07
Patent number
US04851423

Reaction notes

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