Hydrochloric Acid → 2H-Thieno(2,3-e)-1,2-thiazine-3-carboxylic acid, 4-hydroxy-2-methyl-, methyl ester, 1,1-dioxide

HRID 28007

反応式

HRID 28007 の反応式
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+].Cl>>[OH:2][C:3]1[C:5]2[S:6][CH:7]=[CH:8][C:9]=2[S:10](=[O:20])(=[O:19])[N:11]([CH3:12])[C:13]=1[C:14]([O:16][CH3:17])=[O:15]

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 28087943-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl esterHCID 10942334Sodium Methoxide

生成物 1

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

実験手順

13.2 G. (0.041 mol) of the obtained 3-(N-carbethoxymethyl-N-methylsulfamoyl)-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 atmosphere, everything dissolving after stirring for 15 minutes. The solution is heated to reflux for 25 minutes, cooled, neutralized with concentrated hydrochloric acid and evaporated in vacuo. The residue is taken up in methylene chloride, shaken out once each time with water and a 5% sodium bicarbonate solution, dried and evaporated. The crystalline residue is digested with a small amount of methanol for purification. There is obtained 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide of melting point 193°-195° C., which can be converted by reaction with 2-aminothiazole in a manner analogous to that described in the last part of Example 1 into the 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of melting point 217° C. (decomposition).

後処理

  1. temperatureThe solution is heated
  2. temperatureto reflux for 25 minutes
  3. temperaturecooled
  4. customevaporated in vacuo
  5. stirringshaken out once each time with water
  6. dry with materiala 5% sodium bicarbonate solution, dried
  7. customevaporated
  8. customThe crystalline residue is digested with a small amount of methanol for purification

出典と根拠

ORDレコード
ord-078633614ae54eb0863ddf29a1ba60b0
出典データセット
uspto-grants-1980_09
特許番号
US04224445

関連ノート

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