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

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+1]+.

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

ORD-Eintrag

ord-bcf30479e539497596e4a25fd73b9fe1

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08940726B2