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Pyridine → N-[3-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide

HRID 483560
ノート
印刷プレビュー

反応式

HRID 483560 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].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)Cl>C(Cl)Cl.O>[OH:6][CH2:5][C:4]1[CH:3]=[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:9]=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1049PyridineHCID 6212ChloroformHCID 802933-Aminobenzyl alcoholHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

生成物 1

HCID 10003333N-[3-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide収率 82.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 8.17 g of m-aminobenzyl alcohol and 16.14 g of pyridine in 200 ml of methylene chloride is added at 0° C. over 30 minutes a solution of 18 g of p-tetradecyloxybenzoyl chloride in 200 ml of methylene chloride. Stirring is continued for another 6 hours. An additional 400 ml of chloroform and water is added followed by warming to dissolve all the solids. The warm organic layer is separated and washed with dilute hydrochloric acid and saturated sodium bicarbonate. The warm organic layer is dried and filtered. The filtrate is diluted with an equal volume of hexane and cooled in a refrigerator overnight. The resulting solid is collected and air dried to give 18.4 g of the desired product as a white solid, m.p. 112°-115° C.

後処理

  1. temperatureby warming
  2. dissolutionto dissolve all the solids
  3. customThe warm organic layer is separated
  4. washwashed with dilute hydrochloric acid and saturated sodium bicarbonate
  5. customThe warm organic layer is dried
  6. filtrationfiltered
  7. additionThe filtrate is diluted with an equal volume of hexane
  8. temperaturecooled in a refrigerator overnight
  9. customThe resulting solid is collected
  10. customair dried

出典と根拠

ORDレコード
ord-ee6686cdafc5499fad2c7154160a53da
出典データセット
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05225425

反応ノート

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