Sodium Hydroxide → 5-Chloro-2-(3-fluorophenyl)-4H-3,1-benzoxazin-4-one

HRID 652813Notes

Reaction equation

HRID 652813 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].[F:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=O.[OH-].[Na+].S(Cl)(Cl)=O>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.ClCCCl>[Cl:1][C:2]1[C:7]2[C:8](=[O:10])[O:9][C:16]([C:15]3[CH:19]=[CH:20][CH:21]=[C:13]([F:12])[CH:14]=3)=[N:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 743763-Fluorobenzoyl chlorideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 128371115-Chloro-2-(3-fluorophenyl)-4H-3,1-benzoxazin-4-oneYield 99.9%

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

When 42.9 g of 6-chloroanthranilic acid, 39.6 g of 3-fluorobenzoyl chloride, 20 g of 50% strength sodium hydroxide solution, 0.45 g of benzyltriphenylphosphonium chloride, 620 g of 1,2-dichloroethane and 32.7 g of thionyl chloride are used as starting materials and the procedure described in Example 1 is employed, 68.8 g of 5-chloro-2-(m-fluorophenyl)-4H-3,1-benzoxazin-4-one of melting point 120°-123° C. are obtained. The yield is virtually quantitative and the purity is 98% according to HPLC.

Sources & evidence

ORD record
ord-7473931e569149afacb532134d0b4a13
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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