2-Chlorobutanoyl chloride → 4H-3,1-Benzoxazin-4-one, 2-(1-chloropropyl)-8-(trifluoromethyl)-

HRID 1153814Notes

Reaction equation

HRID 1153814 reaction equation
[Cl:1][CH:2]([CH2:6][CH3:7])[C:3](Cl)=[O:4].[NH2:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12]>C1(C)C=CC=CC=1>[Cl:1][CH:2]([C:3]1[O:4][C:11](=[O:12])[C:10]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([F:19])([F:20])[F:21])[C:9]=2[N:8]=1)[CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 1390532-Chlorobutanoyl chlorideHCID 6045692-Amino-3-(trifluoromethyl)benzoic acid

Product 1

HCID 134230814H-3,1-Benzoxazin-4-one, 2-(1-chloropropyl)-8-(trifluoromethyl)-Yield 97.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 20.3 g of 2-chloro-butyryl chloride and 12.3 g of 2-amino-3-trifluoromethyl-benzoic acid in toluene was refluxed under reduced pressure for one hour and was then evaporated to dryness under reduced pressure. The oil residue was added to 100 ml of iced water and the mixture was stirred for one hour and was vacuum filtered. The product was washed with water and dried under reduced pressure at 50° C. to obtain 17 g of 2-(1-chloropropyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-one melting at 65°-70° C.

Workup

  1. temperaturewas refluxed under reduced pressure for one hour
  2. customwas then evaporated to dryness under reduced pressure
  3. additionThe oil residue was added to 100 ml of iced water
  4. filtrationfiltered
  5. washThe product was washed with water
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-292bcb4bd39748af8ec74b9712f80907
Source dataset
uspto-grants-1984_12
Patent number
US04486438

Reaction notes

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