Chloroacetyl chloride → 8-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 2175217Notes

Reaction equation

HRID 2175217 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].C(=O)(O)[O-].[Na+].Cl[CH2:16][C:17](Cl)=[O:18]>C(#N)C.O.CCOC(C)=O>[Br:8][C:4]1[C:3]2[O:9][CH2:16][C:17](=[O:18])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 155315062-Amino-6-bromophenol

Product 1

HCID 218735338-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-6-bromophenol (1 g, 5.32 mmol) in acetonitrile (10 mL) and water (10 mL) was added sodium bicarbonate (1.028 g, 12.23 mmol). The mixture was cooled to 0° C. and chloroacetyl chloride (0.554 mL, 6.91 mmol) was added dropwise. The reaction was refluxed overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (1.14 g, 94% yield) as a dark brown solid. 1H NMR (400 MHz, CDCl3) δ 8.22 (br. s, 1H), 7.23 (dd, J=8.0, 1.4 Hz, 1H), 6.86 (t, J=8.0 Hz, 1H), 6.76 (dd, J=7.9, 1.3 Hz, 1H), 4.74 (s, 2H).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. temperatureAfter cooling to room temperature
  3. washwashed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3380e3769174ad9b564c6279e138203
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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