3-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester → 2H-Thieno(2,3-e)-1,2-thiazine-3-carboxylic acid, 4-hydroxy-2-methyl-, methyl ester, 1,1-dioxide

HRID 2163457Notes

Reaction equation

HRID 2163457 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:20])(=[O:19])[N:11]([CH2:13][C:14]([O:16][CH2:17]C)=[O:15])[CH3:12])=O.C[O-].[Na+]>>[C:14]([C:13]1[N:11]([CH3:12])[S:10](=[O:20])(=[O:19])[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]=1[OH:2])([O:16][CH3:17])=[O:15]

Participants

3

Reactant 2

HCID 28087943-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 546905992H-Thieno(2,3-e)-1,2-thiazine-3-carboxylic acid, 4-hydroxy-2-methyl-, methyl ester, 1,1-dioxide

Procedure

13.2 G. of 3-(N-carbethoxymethyl-N-methyl-sulfamoyl)-thiophene-2-carboxylic acid methyl ester are suspended in 42 ml. of a 1-N methanolic sodium methylate solution in the cold and under a nitrogen stream. After stirring for 15 minutes, a clear solution results. The solution is heated to reflux for 20 minutes, then cooled, neutralized and evaporated in vacuo. The residue is taken up in methylene chloride, shaken once each time with water and a sodium bicarbonate solution, dried and evaporated. The residue is brought to crystallization with methanol. There is obtained 3-carbomethoxy-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide of melting point 193°-195° C.

Workup

  1. customa clear solution results
  2. temperatureThe solution is heated
  3. temperatureto reflux for 20 minutes
  4. temperaturecooled
  5. customevaporated in vacuo
  6. stirringshaken once each time with water
  7. dry with materiala sodium bicarbonate solution, dried
  8. customevaporated
  9. customThe residue is brought to crystallization with methanol

Sources & evidence

ORD record
ord-b007d65d5378424aa4cb2fdb7cb4a0ee
Source dataset
uspto-grants-1979_01
Patent number
US04134898

Reaction notes

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