Hydrochloric Acid → 2-(Dichloromethyl)-8-(trifluoromethyl)-4H-3,1-benzoxazin-4-one

HRID 434529

Reaction equation

HRID 434529 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]([Cl:20])[C:17](Cl)=O.Cl>>[Cl:15][CH:16]([Cl:20])[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

Participants

4

Reactant 3

HCID 313Hydrochloric Acid3×HCID 6593Dichloroacetyl chlorideHCID 6045692-Amino-3-(trifluoromethyl)benzoic acid

Product 1

HCID 133813212-(Dichloromethyl)-8-(trifluoromethyl)-4H-3,1-benzoxazin-4-oneYield 94%

Conditions

Temperature
50 °C

Procedure

A mixture of 17.44 g of 2-amino-3-trifluoromethylbenzoic acid prepared by the process of J. Med. Chem., Vol. 16 (2) (1973), p. 101-106 and 34.63 g of dichloroacetyl chloride was progressively heated with stirring and at about 50° C., a hardening of the mass with rapid gas evolution of regular hydrogen chloride occured for one hour. Towards 100° C., one observed a fluidization of the reaction mixture, an intensification of hydrogen chloride evolution and an increase in the temperature of 127° C. The heating was continued until hydrogen chloride evolution ceased to obtain a brown solution which was cooled in an ice bath with stirring. The mixture was vacuum filtered and the product was empasted with ether, then with methanol and was washed with methanol to obtain 23.82 g of 2-dichloromethyl-8-trifluoromethyl-4H-3,1-benzoxazine-4-one melting at 179° C.

Workup

  1. customprepared by the process of J
  2. customTowards 100° C., one
  3. customto obtain a brown solution which
  4. temperaturewas cooled in an ice bath
  5. stirringwith stirring
  6. filtrationfiltered
  7. washwith methanol and was washed with methanol

Sources & evidence

ORD record
ord-85126f8e39e74c9b851eab31d64ace87
Source dataset
uspto-grants-1983_08
Patent number
US04397856

Linked notes

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