Chloroacetyl chloride → HCID 86727383, compound

HRID 519218Notes

Reaction equation

HRID 519218 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([F:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C([O-])(O)=O.[Na+].CC(C)[CH2:20][C:21](=[O:23])C.ClCC(Cl)=O>O>[C:8]([C:6]1[C:5]([F:11])=[CH:4][C:3]2[O:12][CH2:20][C:21](=[O:23])[NH:1][C:2]=2[CH:7]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 7909Methyl Isobutyl KetoneHCID 516892Sodium BicarbonateHCID 867273811-(5-Amino-2-fluoro-4-hydroxyphenyl)ethanone

Product 1

HCID 86727383HCID 86727383, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(5-amino-2-fluoro-4-hydroxy-phenyl)-ethanone (13.2 g, 78 mmol), NaHCO3 (19.67 g, 234 mmol) in water (90 mL), and 4-methyl-2-pentanone (90 mL) at 0° C. was added 2-chloroacetyl chloride (13.22 g, 8.8 mL, 117 mmol) dropwise. After addition, the reaction mixture was stirred at ambient temperature for 0.5 h and then at 80° C. for 18 h. The mixture was cooled to ambient temperature and filtered to give 6-acetyl-7-fluoro-4H-benzo[1,4]oxazin-3-one as gray solid (12 g, 74%), which was used in next step directly without further purification. 1H NMR (DMSO-d6, 400 MHz): δ 10.90 (s 1H), 7.35 (d, J=7.6 Hz, 1H), 7.02 (d, J=11.6 Hz, 1H), 4.71 (s, 2H), 2.47 (d, J=4.8 Hz, 3H).

Workup

  1. additionAfter addition
  2. waitat 80° C. for 18 h
  3. temperatureThe mixture was cooled to ambient temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1c8f074791a548119323b08f9f03e9d5
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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