Bromoacetonitrile → HCID 86663252, compound

HRID 1697383Notes

Reaction equation

HRID 1697383 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH3:14][CH2:15][N:16](C(C)C)C(C)C.BrCC#N>C1COCC1>[C:15]([CH2:14][NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])#[N:16]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 13399999Methyl 3-amino-4-ethylbenzoate

Product 1

HCID 86663252HCID 86663252, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-amino-4-ethylbenzoate (6.10 g) in THF (56.7 mL) at room temperature was added Hunig's Base (11.89 mL) followed by bromoacetonitrile (4.74 mL). The mixture was heated at reflux for 16 h. The reaction was cooled to room temperature and concentrated in vacuo. 1N aqueous HCl and DCM were added. The organic layer was separated, dried (MgSO4) and concentrated to give the subtitle compound as an oil (7.46 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. addition1N aqueous HCl and DCM were added
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d6222e5a33c7444db9eb12c577f41ed4
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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