Chloroacetyl chloride → 5-Hydroxy-2H-1,4-benzoxazin-3(4H)-one

HRID 1777168Notes

Reaction equation

HRID 1777168 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].Cl[CH2:11][C:12](Cl)=[O:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[OH:8][C:7]1[C:2]2[NH:1][C:12](=[O:13])[CH2:11][O:9][C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 694512-Aminoresorcinol

Product 1

HCID 457898075-Hydroxy-2H-1,4-benzoxazin-3(4H)-oneYield 64.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-aminobenzene-1,3-diol (2.0 g, 16.0 mmol) and TEA (1.94 g, 19.2 mmol) in anhydrous DMF (30 mL) was treated with 2-chloroacetyl chloride (1.81 g, 16.0 mmol) and stirring continued for 16 h at room temperature, then K2CO3 (2.65 g, 19.2 mmol) was added and the mixture further stirred for 16 h at the same temperature. The reaction mixture was diluted with DCM (100 mL), washed twice with water and then with brine, dried over anhydrous Na2SO4, filtered and concentrated. The resulting residue was purified by chromatographic column of silicagel to give desired product (1.7 g, 64% yield) LCMS (m/z): 166.1 [M+H]+.

Workup

  1. stirringthe mixture further stirred for 16 h at the same temperature
  2. washwashed twice with water
  3. dry with materialwith brine, dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by chromatographic column of silicagel

Sources & evidence

ORD record
ord-bde30a27df5b42fbb9b027981e386b24
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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