Chloroacetyl chloride → 7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 519230Notes

Reaction equation

HRID 519230 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C([O-])(O)=O.[Na+].Cl[CH2:16][C:17](Cl)=[O:18]>O.COCCOC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:17](=[O:18])[CH2:16][O:9][C:3]=2[CH:4]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 143206052-Amino-5-bromophenol

Product 1

HCID 143051127-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a mixture of 2-amino-5-bromophenol (51.3 g, 273 mmol) and NaHCO3 (68.8 g, 819 mmol) in water (200 mL) and DME (200 mL) was added 2-chloroacetyl chloride (46.2 g, 409 mmol) at 0° C. and the reaction mixture was stirred at 15° C. for 0.5 h then heated at 80° C. for 18 h. The reaction mixture was cooled to ambient temperature. The precipitate was collected by suction, washed with water and dried in vacuo to give 7-bromo-4H-benzo[1,4]oxazin-3-one (59.7 g, 96%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 10.83 (br s, 1H), 7.17 (s, 1H), 7.12 (d, J=8.4 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 4.59 (s, 2H).

Workup

  1. temperaturethen heated at 80° C. for 18 h
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customThe precipitate was collected by suction
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-560189ed563c401fab2259b37c3c5fb2
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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