Bromoacetonitrile → HCID 86663252, compound

HRID 337124Notes

Reaction equation

HRID 337124 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-3bad7e4eaed14f8fb5fb09d61e769a14
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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