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

HRID 1153806Notes

Reaction equation

HRID 1153806 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

3

Reactant 2

HCID 1110192-Chloropropionyl chlorideHCID 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

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

Sources & evidence

ORD record
ord-56f74fbd68384ec0ab21d683e34ef61f
Source dataset
uspto-grants-1984_12
Patent number
US04486438

Reaction notes

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