m-Chloroperbenzoic acid → HCID 19020474, compound

HRID 1109589Notes

Reaction equation

HRID 1109589 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][S:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[O:1]=[C:2]1[N:7]2[CH2:8][S:9](=[O:33])[C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19020485HCID 19020485, compound

Product 1

HCID 19020474HCID 19020474, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4 g of methyl 7-oxo-8-phenyl-pyrido[1,2-c]thieno[2,3-e][1,3]thiazine-10-carboxylate were dissolved in 100 ml of methylene chloride, whereupon the solution was cooled to 0° and a solution of 2.43 g of m-chloroperbenzoic acid in 40 ml of methylene chloride was added dropwise. After the reaction was completed, the precipitated m-chlorobenzoic acid was removed by filtration and the filtrate was washed with saturated sodium hydrogen carbonate solution and water, dried over sodium sulfate, filtered and evaporated. After chromatography on silica gel, the product was recrystallized from acetonitrile. There was obtained methyl 7-oxo-8-phenyl-pyrido[1,2-c]thieno[2,3-e]-[1,3]thiazine-10-carboxylate 4-oxide as yellow crystals of m.p. 183°-186°.

Workup

  1. temperaturewas cooled to 0°
  2. customthe precipitated m-chlorobenzoic acid was removed by filtration
  3. washthe filtrate was washed with saturated sodium hydrogen carbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customAfter chromatography on silica gel, the product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-f656ea56e52c48c28133bdde4b8aee49
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

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