Ethyl Acetate → HCID 178424717, compound

HRID 337259Notes

Reaction equation

HRID 337259 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14]#[N:15])[CH:9]=[CH:10][C:11]=1[CH3:12].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH2:13][C:14]1[NH:23][N:22]=[N:21][N:15]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 66959086HCID 66959086, compound

Product 1

HCID 178424717HCID 178424717, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(3-(2,6-dimethylbenzyloxy)-4-methylphenyl)acetonitrile (Step B, 1.12 g, 4.2 mmol), sodium azide (0.400 g, 6.1 mmol) and ammonium chloride (0.350 g, 6.5 mmol) in dry DMF (15 ml) was heated under argon at 90° C. for 16 hours or until all the starting material is consumed, the reaction mixture was cooled, diluted with water and extracted with EtOAc (30 ml×4). The combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol 95:5→92.5:7.5) 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. additiondiluted with water
  4. extractionextracted with EtOAc (30 ml×4)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (chloroform:methanol 95:5→92.5:7.5)
  10. customto give semi solid product
  11. filtrationfiltered
  12. customto give product as a white solid

Sources & evidence

ORD record
ord-380de103ebee4e6d9b3da60d002a04c2
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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