Hydrochloric Acid → 4-hydroxy-2-methyl-N-phenyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

HRID 1702625Notes

Reaction equation

HRID 1702625 reaction equation
[CH3:1][N:2]1[CH2:7][C:6](=[O:8])[C:5]2[S:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:4]=2[S:3]1(=[O:17])=[O:16].[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+].Cl>CN(C)C=O>[OH:8][C:6]1[C:5]2[S:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:4]=2[S:3](=[O:17])(=[O:16])[N:2]([CH3:1])[C:7]=1[C:25]([NH:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 205262043,4-dihydro-2-methyl-4-oxo-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide

Product 1

HCID 705451164-hydroxy-2-methyl-N-phenyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
27 °C

Procedure

2.67 g. of 3,4-dihydro-2-methyl-4-oxo-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide are dissolved in 40 ml. of absolute dimethylformamide and 1.2 ml. of phenylisocyanate are added. The solution obtained is added dropwise at 4° C. within 30 minutes to a suspension of 600 mg. of a 55% sodium hydride dispersion in paraffin in 10 ml. of dimethylformamide. The mixture is stirred for a further 1 hour at 4° C. and subsequently for 2 hours at 27° C. and then stirred into 400 ml. of ice/water. The solution obtained is acidified with concentrated hydrochloric acid. The precipitate is filtered off under suction, washed with water and dissolved in methylene chloride. The resulting solution is dried over sodium sulfate and evaporated. The residue is stirred with 30 ml. of methanol. The insoluble components are digested with acetonitrile, filtered off under suction and dried for 4 hours at 100° C./11 Torr. The 4-hydroxy-2-methyl-N-phenyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide obtained melts at 261°-263° C.

Workup

  1. customThe solution obtained
  2. additionis added dropwise at 4° C. within 30 minutes to a suspension of 600 mg
  3. stirringstirred into 400 ml
  4. customThe solution obtained
  5. filtrationThe precipitate is filtered off under suction
  6. washwashed with water
  7. dissolutiondissolved in methylene chloride
  8. dry with materialThe resulting solution is dried over sodium sulfate
  9. customevaporated
  10. stirringThe residue is stirred with 30 ml
  11. filtrationfiltered off under suction
  12. customdried for 4 hours at 100° C./11 Torr

Sources & evidence

ORD record
ord-29e964033d27480eabd3c69ca4537491
Source dataset
uspto-grants-1982_09
Patent number
US04348519

Reaction notes

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