Ammonium Chloride → 5-[[3-(2-Phenyl-4-thiazolylmethoxy)phenyl]methyl]-1H-tetrazole

HRID 330378Notes

Reaction equation

HRID 330378 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][C:21]#[N:22])[CH:17]=[CH:18][CH:19]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].C(OCC)(=O)C.CCCCCC>CN(C)C=O.O>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][C:21]4[NH:25][N:24]=[N:23][N:22]=4)[CH:17]=[CH:18][CH:19]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 144799853-(2-Phenyl-4-thiazolylmethoxy)benzenacetonitrileHCID 21226206Ethyl acetate hexane

Product 1

HCID 1784201555-[[3-(2-Phenyl-4-thiazolylmethoxy)phenyl]methyl]-1H-tetrazoleYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 9.0 g (0.03 mol) of 3-(2-phenyl-4-thiazolylmethoxy)benzenacetonitrile in 200 ml of dimethylformamide are added 9.5 g (0.15 mol) of sodium azide and 7.9 g (0.15 mol) of ammonium chloride, and the slurry is heated to 135° C. for 72 hours. The mixture is allowed to cool to room temperature, diluted with 200 ml of water, and extracted four times with 200 ml of ethyl acetate. The combined ethyl acetate solution is washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil, which is subjected to high pressure liquid chromatography (ethyl acetate/hexane as eluent). Fraction 2 is concentrated to obtain 3.0 g (29%) of crystals, m.p. 160°-161° C.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted four times with 200 ml of ethyl acetate
  3. washThe combined ethyl acetate solution is washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain an oil, which
  7. concentrationFraction 2 is concentrated

Sources & evidence

ORD record
ord-88f773cb2c604fd989dc71c87669930c
Source dataset
uspto-grants-1990_01
Patent number
US04895953

Reaction notes

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