Sodium hydride → N-(N-[1-Methoxycarbonylethyl]carbamoyl)-2-phenylethenesulfonamide

HRID 461467

反応式

HRID 461467 の反応式
Cl.[CH3:2][O:3][C:4](=[O:8])[CH:5]([CH3:7])[NH2:6].[H-].[Na+].C1(N(C2C=CC=CC=2)[C:18]([NH:20][S:21]([CH:24]=[CH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:23])=[O:22])=[O:19])C=CC=CC=1.C1(C=CS(N)(=O)=O)C=CC=CC=1>CCOCC.CN(C)C=O>[CH3:2][O:3][C:4]([CH:5]([NH:6][C:18]([NH:20][S:21]([CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:23])=[O:22])=[O:19])[CH3:7])=[O:8]

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 2575012-PhenylethenesulfonamideHCID 2756298Alanine, methyl ester, hydrochloride (1:1)HCID 53928905N-(Diphenylcarbamoyl)-2-phenylethene-1-sulfonamide

生成物 1

HCID 54315961N-(N-[1-Methoxycarbonylethyl]carbamoyl)-2-phenylethenesulfonamide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3.5 g. of DL-alanine methyl ester hydrochloride in 20 ml. of N,N-dimethylformamide is added 1.05 g. of a 56.6% suspension of sodium hydride in mineral oil. The mixture is stirred at ambient temperature for 15 minutes, and then 3.8 g. of N-(N,N-diphenylcarbamoyl)-2-phenylethenesulfonamide is added. The whole reaction mixture is then maintained at ca. 90° C. for 40 minutes. After being allowed to cool to room temperature, it is diluted with an excess of ether and then it is extracted with water. Acidification of the water extract with dilute hydrochloric acid causes precipitation of the crude product, which is then filtered off. The ether phase is washed with dilute hydrochloric acid, which causes a further crop of product to precipitate. It is filtered off and the two crops of product are combined. This yields 1.55 g. of material having a melting point of 135°-139° C. The crude product is recrystallized from a mixture of acetone and hexane, giving 0.70 g. of N-[N-1-methoxycarbonylethyl)carbamoyl]-2-phenylethenesulfonamide, m.p. 138°-140° C.

後処理

  1. customThe whole reaction mixture
  2. temperatureis then maintained at ca. 90° C. for 40 minutes
  3. temperatureto cool to room temperature
  4. extractionit is extracted with water
  5. extractionAcidification of the water extract with dilute hydrochloric acid
  6. customprecipitation of the crude product, which
  7. filtrationis then filtered off
  8. washThe ether phase is washed with dilute hydrochloric acid, which
  9. customto precipitate
  10. filtrationIt is filtered off
  11. customThe crude product is recrystallized from a mixture of acetone and hexane
  12. customgiving 0.70 g

出典と根拠

ORDレコード
ord-fbdc6335ce0c4e079f14a8f6a4bd4bd3
出典データセット
uspto-grants-1977_12
特許番号
US04062960

関連ノート

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