Thionyl Chloride → HCID 14461287, compound

HRID 1589599Notes

Reaction equation

HRID 1589599 reaction equation
S(Cl)(Cl)=O.[F:5][CH:6]([F:26])[O:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[C:11]([NH:13][C:14]1[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:16]([OH:18])=[O:17])=O>ClCCCl>[F:5][CH:6]([F:26])[O:7][C:8]1[CH:9]=[C:10]([C:11]2[O:17][C:16](=[O:18])[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:13]=2)[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13390015HCID 13390015, compound

Product 1

HCID 14461287HCID 14461287, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

25 parts by weight of 3-difluoromethoxybenzoyl chloride and 12.2 parts by weight of triethylamine are added over 15 minutes, from 2 separate feeds, to a stirred mixture of 16.6 parts by weight of anthranilic acid in 360 parts by weight of 1,2-dichloroethane at 25°-30° C. After stirring for 2 hours at 25° C., the reaction mixture is extracted with 0.5 N hydrochloric acid and with water. The organic phase is then extracted with four times 100 parts of 0.5 N sodium hydroxide solution, and the extracts are stirred into dilute hydrochloric acid. After filtration and drying, 30.4 parts by weight, corresponding to 82% of theory, of N-(3-difluoromethoxybenzoyl)-anthranilic acid of melting point 186°-191° C. are obtained. 8.33 Parts by weight of thionyl chloride are introduced into a stirred mixture of 18 parts by weight of N-(3-difluoromethoxybenzoyl)anthranilic acid in 250 parts by weight of 1,2-dichloroethane at 25° C.; the mixture is then stirred for 4 hours under reflux. When it has cooled, the reaction mixture is extracted with 100 parts by volume of ice-water and 100 parts by volume of 0.5 N sodium hydroxide solution and is chromatographed over neutral aluminum oxide. 12 parts by weight, corresponding to 71% of theory, of 2-(3'-difluoromethoxy-phenyl)-3,1-benzoxazin-4-one, of melting point 84°-87° C., are obtained.

Workup

  1. temperatureunder reflux
  2. temperatureWhen it has cooled
  3. extractionthe reaction mixture is extracted with 100 parts by volume of ice-water and 100 parts by volume of 0.5 N sodium hydroxide solution
  4. customis chromatographed over neutral aluminum oxide

Sources & evidence

ORD record
ord-835417f3a3974b33a72179f551dc7498
Source dataset
uspto-grants-1986_02
Patent number
USRE032087

Reaction notes

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