Water → HCID 22993341, compound

HRID 1167622Notes

Reaction equation

HRID 1167622 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][NH:8][C:7]=2[CH:18]=1.O.C(=O)([O-])O.[K+].Br[CH2:26][C:27]#[N:28]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][N:8]([CH2:26][C:27]#[N:28])[C:7]=2[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 516893Potassium BicarbonateHCID 22993353HCID 22993353, compound

Product 1

HCID 22993341HCID 22993341, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
70 °C

Procedure

The compound obtained in Step C (1.5 g; 6.22 mmol) is suspended in 25 ml of water (4 ml/1 mmol). Potassium hydrogen carbonate (10 eq.; 62.2 mmol; 5.22 g), tetrabutylammonium bromide (0.05 eq.; 0.31 mmol; 100 mg) and bromoacetonitrile (8 eq.; 49.7 mmol; 3.46 ml) are then added. The mixture is stirred vigorously at 70° C. for 16 hours. After returning to ambient temperature, the product formed is extracted with dichloromethane. The organic phase is dried over MgSO4, filtered, and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2)). The title product is obtained in the form of a solid.

Workup

  1. customAfter returning to ambient temperature
  2. customthe product formed
  3. extractionis extracted with dichloromethane
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2))

Sources & evidence

ORD record
ord-8cdb001a34634d3aa1e39af1ae29f9d4
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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