Sodium Cyanide → 2-Thiophenepropanenitrile

HRID 1193562ノート

反応式

HRID 1193562 の反応式
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=O)=O)=CC=1.[C-:19]#[N:20].[Na+]>CS(C)=O>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][CH2:11][C:19]#[N:20]

参加物

4

反応物 2

HCID 8929Sodium CyanideHCID 36820342-Thiopheneethanol tosylate

生成物 1

HCID 5664252-Thiophenepropanenitrile

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

A mixture was prepared from 20.8 g of 2-[2-(4-toluenesulfonyloxy)ethyl]thiophene, 5.4 g of sodium cyanide and 175 ml of dimethylsulfoxide and this mixture was heated to 90° C. The mixture was quenched by pouring it into saturated aqueous ammonium chloride solution and the resulting solution was extracted into ethyl acetate. The ethyl acetate solution was dried over sodium sulfate and the solvent was evaporated under reduced pressure to give crude 2-thiophenepropionitrile. This product was mixed with 175 ml of 1M diborane in tetrahydrofuran and allowed to stir at room temperature. The reaction was quenched in ethanol and methanolic hydrogen chloride was added. The white solid which formed was separated by filtration, washed with ether and dried in a vacuum oven to give 3-(2-thienyl)propylamine hydrochloride melting at about 197°-198° C.

後処理

  1. customThe mixture was quenched
  2. additionby pouring it into saturated aqueous ammonium chloride solution
  3. extractionthe resulting solution was extracted into ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-9df6513c618e4ae6bb1becdfa5063efc
出典データセット
uspto-grants-1989_03
特許番号
US04810800

反応ノート

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