Chloroacetyl chloride → 7-Chloro-2H-1,4-benzoxazin

HRID 1710642Notes

Reaction equation

HRID 1710642 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].Cl[CH2:11][C:12](Cl)=[O:13].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:12](=[O:13])[CH2:11][O:9][C:3]=2[CH:4]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 915912-Amino-5-chlorophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 118300867-Chloro-2H-1,4-benzoxazin

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-5-chloro-phenol (27) (2.0 g, 14 mmol, 1 equiv) in 30 ml of THF, chloroacetyl chloride (1.26 ml, 16.8 mmol, 1.2 equiv), and saturated aqueous NaHCO3 50 mL was stirred at RT for 2 hrs and then heated at 80° C. overnight. The reaction mixture was diluted with EtOAc, and washed with water. Purification of the crude product by flash chromatography provided 7-chloro-4H-benzo[1,4]oxazin-3-one (28): LCMS Retention time: 1.48 min.; LCMS observed (M+H)+: 184.

Workup

  1. temperatureheated at 80° C. overnight
  2. washwashed with water
  3. customPurification of the crude product by flash chromatography

Sources & evidence

ORD record
ord-fe26fbf7e13e4c3c935a734864472926
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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