Chloroacetyl chloride → 6,8-Dichloro-7-ethyl-4H-benzo[1,4]oxazin-3-one

HRID 969307

Reaction equation

[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[C:5]([CH2:10][CH3:11])=[C:4]([Cl:12])[CH:3]=1.Cl[CH2:14][C:15](Cl)=[O:16].C([O-])([O-])=O.[K+].[K+]>>[Cl:12][C:4]1[C:5]([CH2:10][CH3:11])=[C:6]([Cl:9])[C:7]2[O:8][CH2:14][C:15](=[O:16])[NH:1][C:2]=2[CH:3]=1

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 11430Potassium Carbonate

HCID 117696522,4-Dichloro-3-ethyl-6-aminophenol

Product 1

HCID 689129296,8-Dichloro-7-ethyl-4H-benzo[1,4]oxazin-3-oneYield 92.1%

Procedure

6-Amino-2.4-dichloro-3-etylphenol (95MF2226) (0.293 g, 1.5 mmol), 2-chloroacetyl chloride (0.19 g, 1.7 mmol) and K2CO3 (0.44 g, 3.2 mmol) were mixed according to GP1 to give the title compound as a crude (95MF46) (0.34 g).

Sources & evidence

ORD record: ord-147da56f85774c1186e82eb6272bbad0
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07307075B2

Linked notes

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