1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → 2-(2-imidazolin-2-yl)-1-phenyl-1H-indole

HRID 1770121ノート

反応式

HRID 1770121 の反応式
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]#[N:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:29](N)[CH2:30][NH2:31]>>[NH:17]1[CH2:29][CH2:30][N:31]=[C:16]1[C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

参加物

3

反応物 2

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 20095505HCID 20095505、化合物

生成物 1

HCID 102208542-(2-imidazolin-2-yl)-1-phenyl-1H-indole

反応条件

温度
200 °C

実験手順

A stirred mixture of 1-phenyl-1H-indole-2-carbonitrile (15 g) and ethylenediamine monotosylate (17.6 g) was heated at 200° C. for 2 hours. After cooling, the reaction mixture was partitioned between toluene (100 ml) and dilute hydrochloric acid (400 ml). The aqueous layer was extracted with diethyl ether, cooled in an ice bath then basified with concentrated ammonia and reextracted with dichloromethane. The combined dichloromethane extracts were washed with water, dried and the solvent removed in vacuo. The residue was purified by chromatography on neutral alumina (grade III) eluting with 1% methanol in dichloromethane, followed by trituration with toluene to give 2-(2-imidazolin-2-yl)-1-phenyl-1H-indole as a white solid: yield 16.6 g (90%); mp 180.5°-182° C. The hydrochloride salt was prepared as described above: yield 16.3 g (95%); mp 263.5°-265.5° C.

後処理

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between toluene (100 ml) and dilute hydrochloric acid (400 ml)
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. temperaturecooled in an ice bath
  5. washThe combined dichloromethane extracts were washed with water
  6. customdried
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by chromatography on neutral alumina (grade III)
  9. washeluting with 1% methanol in dichloromethane

出典と根拠

ORDレコード
ord-3e801975a1254b6baff85c21d1498fbe
出典データセット
uspto-grants-1995_01
特許番号
US05385919

反応ノート

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