Thionyl Chloride → HCID 12837112, compound

HRID 1902391Notes

Reaction equation

HRID 1902391 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:24]=[CH:23][C:9]([C:10]([NH:12][C:13]2[C:14](=[C:18]([Cl:22])[CH:19]=[CH:20][CH:21]=2)[C:15]([OH:17])=[O:16])=O)=[CH:8][CH:7]=1>ClCCCl>[F:5][C:6]1[CH:24]=[CH:23][C:9]([C:10]2[O:16][C:15](=[O:17])[C:14]3[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:13]=3[N:12]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12837109HCID 12837109, compound

Product 1

HCID 12837112HCID 12837112, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

15.5 parts of thionyl chloride are added to a suspension of 29 parts of N-(4'-fluorobenzoyl)-6-chloroanthranilic acid in 250 parts of 1,2-dichloroethane at room temperature, and the mixture is then stirred for one hour under reflux. Thereafter, it is evaporated down and the residue is taken up in methylene chloride; this solution is extracted once with water, and then with twice 100 parts by volume of 0.5 N sodium hydroxide solution. Thereafter, it is dried, chromatographed on neutral alumina and evaporated down, 22.5 parts of 2-(4'-fluorophenyl)-5-chloro-4H-3,1-benzoxazin-4-one, of melting point 159°-162° C., being isolated; yield: 82.7%.

Workup

  1. temperatureunder reflux
  2. customThereafter, it is evaporated down
  3. extractionthis solution is extracted once with water
  4. customThereafter, it is dried
  5. customchromatographed on neutral alumina
  6. customevaporated down

Sources & evidence

ORD record
ord-b625aafd008f4a568c21d68b607452f1
Source dataset
uspto-grants-1982_12
Patent number
US04363651

Reaction notes

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