2-Chloropropionyl chloride → 2-(1-Chloroethyl)-8-fluoro-4H-3,1-benzoxazin-4-one

Reaction equation

[NH2:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][CH:13]([CH3:17])[C:14](Cl)=O>>[Cl:12][CH:13]([C:17]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:2]=2[N:1]=1)[CH3:14]

Participants

Reactant 2

HCID 1110192-Chloropropionyl chloride

HCID 5864082-Amino-3-fluorobenzoic acid

Product 1

HCID 201456912-(1-Chloroethyl)-8-fluoro-4H-3,1-benzoxazin-4-one

Procedure

A mixture of 9.3 g of 2-amino-3-fluoro-benzoic acid and 18,6 ml of α-chloropropionyl chloride was refluxed for 3 hours and excess acid chloride was distilled off. The residue was concentrated under reduced pressure at 70° C. for 2 hours to obtain 2-(1-chloroethyl)-8-fluoro-4H-3,1-benzoxazine-4-one which was used as is for the next step.

Workup

temperaturewas refluxed for 3 hours
distillationexcess acid chloride was distilled off
concentrationThe residue was concentrated under reduced pressure at 70° C. for 2 hours

Sources & evidence

ORD record: ord-f7287818079c4135a8e79bd5d4bdbf3c
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04736033

Reaction notes

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