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

HRID 616829

반응식

HRID 616829 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9b02d0a7604d45a9a6d841806e43af20
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04076709

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