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

HRID 1761674
Notes
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Reaction equation

HRID 1761674 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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-ec6b9639285f4630a279d78523f0e80c
Source dataset
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04826990

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes