Ethyl iodoacetate → 3-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester

HRID 28006

反応式

HRID 28006 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:14])(=[O:13])[NH:11][CH3:12])=[O:4].[H-].[Na+].[CH2:17]([O:19][C:20](=[O:23])[CH2:21]I)[CH3:18]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:14])(=[O:13])[N:11]([CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:23])[CH3:12])=[O:4]

参加物

5

反応物 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 12906749methyl 3-(N-methylsulfamoyl)thiophene-2-carboxylate

生成物 1

HCID 28087943-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

43.5 G. (0.184 mol) of the obtained 3-methylsulfamoyl-thiophene-2-carboxylic acid methyl ester are dissolved in 400 ml. of absolute dimethylformamide are added dropwise at 0° C. during 1 hour to a stirred suspension of 4.5 g. (0.187 mol) of sodium hydride in 50 ml. of absolute dimethylformamide. Then, 40 g. (0.187 mol) of iodoacetic acid ethyl ester dissolved in 50 ml. of absolute dimethylformamide are added dropwise during 2 hours while cooling at 0°-5° C. and the mixture allowed to react for a further 1 hour [until a moistened pH paper shows a pH of 7-8]. The mixture is evaporated in vacuo and the residue taken up with 300 ml. of 0.5-N hydrochloric acid and 300 ml. of methylene chloride. The organic phase is separated, the aqueous phase is back-extracted twice with a small amount of methylene chloride and the combined organic phases are shaken out twice with 100 ml. each time of a 5% sodium bicarbonate solution [the aqueous phases are back-extracted once each time with a small amount of methylene chloride]. The combined organic phases are dried over sodium sulfate and evaporated. The crystalline residue is digested with a small amount of cold ethanol for purification. There is obtained 3-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester of melting point 83°-85° C.

後処理

  1. temperaturewhile cooling at 0°-5° C.
  2. customto react for a further 1 hour [until a moistened pH paper
  3. customThe mixture is evaporated in vacuo
  4. customThe organic phase is separated
  5. extractionthe aqueous phase is back-extracted twice with a small amount of methylene chloride
  6. extractioneach time of a 5% sodium bicarbonate solution [the aqueous phases are back-extracted once each time with a small amount of methylene chloride]
  7. dry with materialThe combined organic phases are dried over sodium sulfate
  8. customevaporated
  9. customThe crystalline residue is digested with a small amount of cold ethanol for purification

出典と根拠

ORDレコード
ord-6123c89ad00749f78063975a5e9d3e64
出典データセット
uspto-grants-1980_09
特許番号
US04224445

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