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

HRID 1505210Notes

Reaction equation

HRID 1505210 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][C:8]=1[OH:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:13][C:12]1[C:7]2[NH:6][C:3](=[O:4])[CH2:2][O:14][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 694512-Aminoresorcinol

Product 1

HCID 457898075-Hydroxy-2H-1,4-benzoxazin-3(4H)-oneYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TEA (3.34 ml, 2 equiv.) and after chloroacetyl chloride (1.15 ml, 1.2 equiv.) were added dropwise to a solution of commercially available 2-aminobenzene-1,3-diol (1.5 g, 11.99 mmol) in 20 ml of DMF. After one hours of stirring at room temperature, K2CO3 (3.3 g, 2 equiv.) was added and the reaction was stirred at room temperature overnight. The solvent was evaporated and to the residue water was added. After filtration, the solid material was washed with MeOH and diethyl ether giving 410 mg of a grey solid. Yield=21% 1HNMR (DMSO, 200 MHz) δ 3.47 (1H, bs), 4.47 (2H, s), 6.44 (2H, m), 6.72 (1H, t, J=8 Hz)

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe solvent was evaporated and to the residue water
  3. additionwas added
  4. filtrationAfter filtration
  5. washthe solid material was washed with MeOH and diethyl ether giving 410 mg of a grey solid

Sources & evidence

ORD record
ord-d696600dc803456583d9c3c8fefcbe2e
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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