Hydrochloric Acid → HCID 19020465, compound

HRID 648546Notes

Reaction equation

HRID 648546 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][S:10][C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:6]2=[C:5]([C:16]([O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[O:17])[CH:4]=[C:3]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.[Cl:31]C1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl>[ClH:31].[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][S:10](=[O:39])[C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:6]2=[C:5]([C:16]([O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[O:17])[CH:4]=[C:3]1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70297m-Chloroperbenzoic acidHCID 14770181HCID 14770181, compound

Product 1

HCID 19020465HCID 19020465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

3.8 g of 2-(dimethylamino)ethyl 5,6-dihydro-8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepine-11-carboxylate in 90 ml of methylene chloride were treated with 9 ml of 3N ethanolic hydrochloric acid, whereupon the mixture was cooled to -10° C. The mixture was treated dropwise with 1.72 g of about 90 percent m-chloroperbenzoic acid in 45 ml of methylene chloride. After warming to room temperature, the mixture was washed with 100 ml of 5 percent sodium hydrogen carbonate solution, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by chromatography on silica gel and then dissolved in 34 ml of methylene chloride. After the addition of 3N ethanolic hydrochloric acid until an acidic reaction was obtained, the mixture was stirred at room temperature for an additional 15 minutes. After removal of the solvent in vacuo and recrystallization from methanol, there was obtained 2-(dimethylamino)ethyl 5,6-dihydro-8-oxo-9-phenyl-8-H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepine-11-carboxylate 4-oxide hydrochloride as yellow crystals of m.p. 148°-152° (dec.).

Workup

  1. temperatureAfter warming to room temperature
  2. washthe mixture was washed with 100 ml of 5 percent sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel
  7. dissolutiondissolved in 34 ml of methylene chloride
  8. additionAfter the addition of 3N ethanolic hydrochloric acid
  9. customuntil an acidic reaction
  10. customwas obtained
  11. customAfter removal of the solvent
  12. customin vacuo and recrystallization from methanol

Sources & evidence

ORD record
ord-8fd41a52b3124edba5b87f6287ddc537
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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