Sodium Hydroxide → 6-fluoro-2-(m-trifluoromethylphenyl)-4H-3,1-benzoxazin-4one

HRID 652819Notes

Reaction equation

HRID 652819 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+].[F:16][C:17]1[CH:25]=[C:21]([C:22](O)=[O:23])[C:20]([NH2:26])=[CH:19][CH:18]=1.S(Cl)(Cl)=O>[Cl-].C[N+](C)(C)CC1C=CC=CC=1.ClCCCl>[F:16][C:17]1[CH:18]=[CH:19][C:20]2[N:26]=[C:6]([C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=3)[O:7][C:22](=[O:23])[C:21]=2[CH:25]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 676063-(Trifluoromethyl)benzoyl fluorideHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 136905086-fluoro-2-(m-trifluoromethylphenyl)-4H-3,1-benzoxazin-4oneYield 90%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Under the reaction conditions described in Example 1, 14.4 g of m-trifluoromethylbenzoyl fluoride, 6 g of 50% strength aqueous sodium hydroxide solution, 11.6 g of 5-fluoroanthranilic acid and 0.15 g of trimethylbenzylammonium chloride in 185 g of 1,2-dichloroethane are reacted with one another, and the product is then subjected to a cyclization reaction with 11 parts of thionyl chloride. Working up the mixture gives 20.8 g (90%) of 6-fluoro-2-(m-trifluoromethylphenyl)-4H-3,1-benzoxazin-4one of melting point 118°-119° C.

Workup

  1. customUnder the reaction conditions
  2. customare reacted with one another, and the product

Sources & evidence

ORD record
ord-b667d37f851349c9af7fa23978e597ee
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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