Bromoacetyl bromide → 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

HRID 255216Notes

Reaction equation

HRID 255216 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C(=O)(O)[O-].[Na+].Br[CH2:17][C:18](Br)=[O:19]>C(Cl)(Cl)Cl>[O:19]=[C:18]1[NH:1][C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=2[O:10][CH2:17]1

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 2712583-amino-4-hydroxybenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 106548133-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared similarly to literature procedure (Caliendo, G; et. al.; Bioorg. Med Chem. Lett., 2002, 10, 2663), but in one step. Commercially available 3-amino-4-hydroxybenzonitrile (2.5 g, 18.6 mmol) was dissolved in chloroform (300 mL) and saturated sodium bicarbonate (90 mL). The biphasic reaction mixture was cooled to 0° C. and bromoacetyl bromide (2.4 mL, 28 mmol) was added dropwise. The reaction was stirred overnight at room temperature. The layers were separated and the aqueous layer was filtered to yield the desired product as a tan solid, 2.3 g (69%).

Workup

  1. customThe title compound was prepared similarly to literature procedure (Caliendo, G; et. al.; Bioorg. Med Chem. Lett., 2002, 10, 2663)
  2. customThe biphasic reaction mixture
  3. customThe layers were separated
  4. filtrationthe aqueous layer was filtered

Sources & evidence

ORD record
ord-2d6ab6793fa649c2bbb16360e088a709
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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