Sodium Methoxide → 3-carbomethoxy-4-hydroxy-2-methyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide

HRID 128258Notes

Reaction equation

HRID 128258 reaction equation
C[O-].[Na+].[CH2:4]([O:6][C:7]([CH2:9][N:10]([CH3:27])[S:11]([C:14]1[C:15]2[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=2[S:17][C:18]=1[C:19](OC)=[O:20])(=[O:13])=[O:12])=[O:8])C>CO>[OH:20][C:19]1[C:18]2[S:17][C:16]3[CH:23]=[CH:24][CH:25]=[CH:26][C:15]=3[C:14]=2[S:11](=[O:13])(=[O:12])[N:10]([CH3:27])[C:9]=1[C:7]([O:6][CH3:4])=[O:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 23468720Methyl 3-{[(ethoxycarbonylmethyl)-methylamino]sulfonyl}-benzo[b]thiophene-2-carboxylate

Product 1

HCID 547072593-carbomethoxy-4-hydroxy-2-methyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

42.0 gm (0.78 mol) of solid sodium methylate were added in an inert gas atmosphere to a suspension of 286 gm (0.77 mol) of methyl 3-{[(ethoxycarbonylmethyl)-methylamino]sulfonyl}-benzo[b]thiophene-2-carboxylate in 1000 cc of anhydrous methanol. The mixture was stirred for 30 minutes at room temperature and then refluxed for 1 hour. The solvent was distilled off, and the residue was stirred into 500 ml of ice-cold 2 N hydrochloric acid. The precipitated product was filtered off, taken up in 400 cc of chloroform, and the solution was dried over sodium sulfate and evaporated in vacuo. After recrystallizing the residue twice from 100 cc each of methanol, 116 gm (46% of theory) of light-yellow crystals were obtained.

Workup

  1. temperaturerefluxed for 1 hour
  2. distillationThe solvent was distilled off
  3. stirringthe residue was stirred into 500 ml of ice-cold 2 N hydrochloric acid
  4. filtrationThe precipitated product was filtered off
  5. dry with materialthe solution was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customAfter recrystallizing the residue twice from 100 cc each of methanol, 116 gm (46% of theory) of light-yellow crystals
  8. customwere obtained

Sources & evidence

ORD record
ord-1b0b393c1a9247a9b29693d3ad2173b8
Source dataset
uspto-grants-1981_03
Patent number
US04259336

Reaction notes

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