Pyridine → N-[4-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide

HRID 653802

反応式

HRID 653802 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:16]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl.C(Cl)(Cl)Cl>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:35](=[O:36])[C:34]2[CH:33]=[CH:32][C:31]([O:30][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:39][CH:38]=2)=[CH:3][CH:4]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 693314-Aminobenzyl alcoholHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

生成物 1

HCID 10410958N-[4-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide収率 67.6%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of 9.75 g of p-aminobenzyl alcohol and 19.27 g of pyridine in 230 ml of methylene chloride cooled to 0° C. is added over 35 minutes a solution of 21.5 g of 4-tetradecyloxybenzoyl chloride in 230 ml of methylene chloride. The mixture is stirred at room temperature for 2 hours and diluted with chloroform. The mixture is heated to dissolve insolubles, washed with hot water and hot dilute hydrochloric acid then dried. The mixture is filtered hot and the solvent evaporated to a residue which is crystallized from tetrahydrofuran:hexane to give 18.1 g of the desired product as a yellow powder, m.p. 140°-145° C.

後処理

  1. temperatureThe mixture is heated
  2. dissolutionto dissolve insolubles
  3. washwashed with hot water and hot dilute hydrochloric acid
  4. customthen dried
  5. filtrationThe mixture is filtered hot
  6. customthe solvent evaporated to a residue which
  7. customis crystallized from tetrahydrofuran

出典と根拠

ORDレコード
ord-62b2fa0731bc4ad183ed9191146be458
出典データセット
uspto-grants-1992_07
特許番号
US05128351

関連ノート

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