Sodium Hydroxide → HCID 20196967, compound

HRID 652814Notes

Reaction equation

HRID 652814 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].[Cl:12][C:13]1[C:14]([O:22][CH:23]([F:25])[F:24])=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](F)=O.[OH-].[Na+].S(Cl)(Cl)=O>[Cl-].C([N+](C)(C)C)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]([Cl:12])[C:14]=3[O:22][CH:23]([F:25])[F:24])=[N:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 750712-Amino-6-chlorobenzoic acidHCID 20196974HCID 20196974, compound

Product 1

HCID 20196967HCID 20196967, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

When 42.9 g of 6-chloroanthranilic acid, 58.4 g of 3-chlorodifluoromethoxybenzoyl fluoride, 20.8 g of 50% strength sodium hydroxide solution, 0.45 g of benzyltrimethylammonium chloride, 700 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, 88.6 g (99%) of 5-chloro-2-(m-chlorodifluoromethoxyphenyl)-4H-3,1-benzoxazin-4-one of melting point 112°-114° C. are obtained.

Sources & evidence

ORD record
ord-3d3e651214464be1b241ead80d19c2d5
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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