Ethyl Acetate → 5-(3-(2,6-Dimethylbenzyloxy)-2-methoxybenzyl)-1H-tetrazole

HRID 337272Notes

Reaction equation

HRID 337272 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([O:15][CH3:16])=[C:8]([CH2:12][C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([O:15][CH3:16])=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][C:13]1[NH:24][N:23]=[N:22][N:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 669593842-(3-(2,6-Dimethylbenzyloxy)-2-methoxyphenyl)acetonitrile

Product 1

HCID 1784882555-(3-(2,6-Dimethylbenzyloxy)-2-methoxybenzyl)-1H-tetrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(3-(2,6-dimethylbenzyloxy)-2-methoxyphenyl)acetonitrile (Step D, 3.2 g, 12.7 mmol), sodium azide (0.86 g, 13.2 mmol) and ammonium chloride (0.696 g, 13.0 mmol) in dry DMF (10 ml) was heated under argon at 90° C. for 16 hours or until all the starting material is consumed, the reaction mixture was cooled, and concentrated under reduced pressure and purified by flash chromatography on a silica gel column (chloroform:methanol 9:1) to give semi solid product. The semi solid was stirred with 1:2 ethyl acetate:hexane (15 ml) for 10 minutes, and filtered to give product as a white solid.

Workup

  1. customis consumed
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash chromatography on a silica gel column (chloroform:methanol 9:1)
  5. customto give semi solid product
  6. filtrationfiltered
  7. customto give product as a white solid

Sources & evidence

ORD record
ord-e1d02a7ed127484bbb5ca71216b1c434
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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