Hydrochloric Acid → HCID 70546988, compound

HRID 1702624Notes

Reaction equation

HRID 1702624 reaction equation
[C:1]([C:5]1[NH:6][S:7](=[O:20])(=[O:19])[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:9]=2[C:10]=1[OH:11])([O:3][CH3:4])=[O:2].[H-].[Na+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.Cl>CN(C)C=O>[C:1]([C:5]1[N:6]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[S:7](=[O:20])(=[O:19])[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:9]=2[C:10]=1[OH:11])([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 70547059HCID 70547059, compound

Product 1

HCID 70546988HCID 70546988, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

935 mg. of 3-carbomethoxy-4-hydroxy-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide are dissolved in 10 ml. of absolute dimethylformamide and 290 mg. of a 55% sodium hydride dispersion in paraffin are added. The suspension is stirred at room temperature for 1 hour. Then, a solution of 730 mg. of 4-methoxybenzyl bromide in 5 ml. of absolute dimethylformamide is added dropwise within 30 minutes, the mixture is stirred at room temperature for a further 3 hours and then poured into 100 ml. of ice-cold water while stirring. The mixture is then acidified to pH 2 with concentrated hydrochloric acid. The precipitate which results is filtered off under suction and dissolved in methylene chloride. The solution is dried over sodium sulfate, filtered and evaporated. The residue crystallizes from methylene chloride after the addition of petroleum ether. The 3-carbomethoxy-4-hydroxy-2-(4-methoxybenzyl)-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide obtained melts at 163°-164° C.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 3 hours
  2. additionpoured into 100 ml
  3. stirringof ice-cold water while stirring
  4. customThe precipitate which results
  5. filtrationis filtered off under suction
  6. dissolutiondissolved in methylene chloride
  7. dry with materialThe solution is dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue crystallizes from methylene chloride
  11. additionafter the addition of petroleum ether

Sources & evidence

ORD record
ord-ca5c0dc62d9740e48bcf85aef5a3c3f9
Source dataset
uspto-grants-1982_09
Patent number
US04348519

Reaction notes

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