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

HRID 653802

반응식

HRID 653802 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-62b2fa0731bc4ad183ed9191146be458
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05128351

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