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

HRID 1958864Notes

Reaction equation

HRID 1958864 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-42cf63607ae342689454d9d28d5b6574
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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