Ammonia → beta-Amino-beta-(2-naphthyl)acrylonitrile

HRID 918235

反応式

HRID 918235 の反応式
[Na].N.[C:3](#[N:5])[CH3:4].[C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)#[N:7]>C(OCC)C>[NH2:7][C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)=[CH:4][C:3]#[N:5]

参加物

6

反応物 4

HCID 222Ammonia2 回HCID 6342Acetonitrile2 回HCID 119442-NaphthalenecarbonitrileHCID 5360545Sodium

生成物 1

HCID 68142773beta-Amino-beta-(2-naphthyl)acrylonitrile収率 22.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 2.0 grams (0.087 mole) of sodium in 125 milliliters of liquid ammonia was added a solution of 3.67 grams (0.089 mole) of acetonitrile in 10 milliliters of diethyl ether over a period of about five minutes. The reaction mixture was then cooled in a dry ice-acetone bath and a solution of 10.0 grams (0.065 mole) of 2-cyanonaphthalene in a minimum of dry diethyl ether was rapidly added within about five minutes after completion of the acetonitrile addition. The reaction mixture was stirred for about one and one-half hours and the ammonia was then allowed to evaporate. Water was cautiously added to the reaction mixture under nitrogen and the resulting mixture was extracted with diethyl ether. The ether was separated and the residue recrystallized from a mixture of chloroform and hexane. There was obtained 2.8 grams (22% of theoretical) of β-amino-β-(2naphthyl)acrylonitrile, melting point 85°-90°C. By the process described in Dornow et al., Chemische Berichte 82, 254-6 (1949), the β-amino-β-(2-naphthyl)acrylonitrile was hydrolyzed to β-amino-β-(2-naphthyl)acrylamide.

後処理

  1. temperatureThe reaction mixture was then cooled in a dry ice-acetone bath
  2. customto evaporate
  3. additionWater was cautiously added to the reaction mixture under nitrogen
  4. extractionthe resulting mixture was extracted with diethyl ether
  5. customThe ether was separated
  6. customthe residue recrystallized from a mixture of chloroform and hexane

出典と根拠

ORDレコード
ord-7994beaba9a141138201bbf42dec4bc3
出典データセット
uspto-grants-1976_07
特許番号
US03970644

関連ノート

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