Sodium Hydroxide → 5-chloro-2-(m-trifluoromethylphenyl)-4H-3,1-benzoxazin-4-one

HRID 652812Notes

Reaction equation

HRID 652812 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](F)=[O:7].[OH-].[Na+].[Cl:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([NH2:26])[C:22]=1[C:23](O)=[O:24]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1(C)C=CC=CC=1>[Cl:16][C:17]1[C:22]2[C:23](=[O:24])[O:7][C:6]([C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=3)=[N:26][C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 676063-(Trifluoromethyl)benzoyl fluorideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 27985105-chloro-2-(m-trifluoromethylphenyl)-4H-3,1-benzoxazin-4-oneYield 92.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

48 g of 3-trifluoromethylbenzoyl fluoride and 20 g of 50% strength aqueous sodium hydroxide solution are added simultaneously via 2 feed apparatuses in the course of 25 minutes at from 25° to 36° C. to a stirred mixture of 42.9 g of 6-chloroanthranilic acid and 0.45 g of triethylbenzylammonium chloride and 700 g of toluene. Stirring is continued for 90 minutes at 27° C., after which the water is separated off at from 87° to 104° C. After the addition of 32.7 g of thionyl chloride in the course of 15 minutes at 70° C., stirring is continued for 90 minutes at 82° C. The mixture is extracted once with water and once with 0.4 N sodium hydroxide solution, and is evaporated down to give 75 g (92%) of 5-chloro-2-(m-trifluoromethylphenyl)-4H-3,1-benzoxazin-4-one of melting point 116°-120° C.

Workup

  1. customafter which the water is separated off at from 87° to 104° C
  2. additionAfter the addition of 32.7 g of thionyl chloride in the course of 15 minutes at 70° C.
  3. stirringstirring
  4. waitis continued for 90 minutes at 82° C
  5. extractionThe mixture is extracted once with water and once with 0.4 N sodium hydroxide solution
  6. customis evaporated down

Sources & evidence

ORD record
ord-8fa8afec56cb4b439c20622d2cb5e25e
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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