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Hydrochloric Acid → 3,4-di-O-nicotinoyl-N-carbobenzoxydopamine

HRID 5906
ノート
印刷プレビュー

反応式

HRID 5906 の反応式
[C:1]([NH:11][CH2:12][CH2:13][C:14]1[CH:21]=[CH:20][C:18]([OH:19])=[C:16]([OH:17])[CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1>N1C=CC=CC=1>[C:23]([O:17][C:16]1[CH:15]=[C:14]([CH:21]=[CH:20][C:18]=1[O:19][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1)[CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 82604Nicotinoyl chlorideHCID 11108946Benzyl N-[2-(3,4-dihydroxyphenyl)ethyl]carbamate

生成物 1

HCID 1317181713,4-di-O-nicotinoyl-N-carbobenzoxydopamine収率 71.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

19.0 g (66 mmol) of N-carbobenzoxydopamine obtained in Synthetic Example 1-(1) and 37.2 g (209 mmol) of hydrochloride of nicotinoyl chloride were added to 200 ml of pyridine. After stirring at room temperature for 12 hours, the mixture was allowed to react at 35°-40° C. for 2 hours. Then, the reaction mixture was poured into ice and a sodium carbonate solution followed by extraction with chloroform. The resulting extract was dried over anhydrous magnesium sulfate and the solvent was distilled off to obtain crude crystals. The thus-obtained crystals were recrystallized from ethyl acetate/diethyl ether (1:5 by volume) to obtain 23.5 g (yield: 71.6%) of the desired compound in the form of white crystals (m.p. 77°-78° C.).

後処理

  1. customto react at 35°-40° C. for 2 hours
  2. additionThen, the reaction mixture was poured into ice
  3. extractiona sodium carbonate solution followed by extraction with chloroform
  4. extractionThe resulting extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customto obtain crude crystals
  8. customThe thus-obtained crystals were recrystallized from ethyl acetate/diethyl ether (1:5 by volume)

出典と根拠

ORDレコード
ord-904e0eff30db466b8a5980cfec8f75e8
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05246949

反応ノート

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