2-Amino-3-(trifluoromethyl)benzoic acid → 4H-3,1-Benzoxazin-4-one, 2-(1-chlorobutyl)-8-(trifluoromethyl)-

HRID 1982608Notes

Reaction equation

HRID 1982608 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:15][CH:16]([CH2:20][CH2:21][CH2:22]C)[C:17](Cl)=O>C1(C)C=CC=CC=1>[Cl:15][CH:16]([C:17]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([F:12])([F:13])[F:14])[C:2]=2[N:1]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 6045692-Amino-3-(trifluoromethyl)benzoic acidHCID 122132192-Chlorohexanoyl chloride

Product 1

HCID 134230804H-3,1-Benzoxazin-4-one, 2-(1-chlorobutyl)-8-(trifluoromethyl)-Yield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.25 g of 2-amino-3-trifluoromethylbenzoic acid, 20 ml of toluene and 20.3 g of 2-chlorohexanoic acid chloride [prepared according to J. Org. CHem., Vol. 40 (1975), p. 23420] was refluxed for one hour and then toluene and excess acid chloride were removed by distillation. The residue was chromatographed over silica gel and eluted with methylene chloride and then by chromatography under pressure. Elution with a 1-1 ethyl acetate-petroleum ether (b.p.=60°-80° C.) mixture yielded 8.4 g of 2-(1-chlorobutyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-one in the form of an oil which was used as is for the next step.

Workup

  1. temperaturewas refluxed for one hour
  2. customtoluene and excess acid chloride were removed by distillation
  3. customThe residue was chromatographed over silica gel
  4. washeluted with methylene chloride
  5. washElution with a 1-1 ethyl acetate-petroleum ether (b.p.=60°-80° C.) mixture

Sources & evidence

ORD record
ord-798b146fe89c4d82b05f190adabc26ae
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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