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3-Bromo-1-propanol → 3-bromopropyl Methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 34413
ノート
印刷プレビュー

反応式

HRID 34413 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:21](O)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].S(Cl)(Cl)=O.[Br:29][CH2:30][CH2:31][CH2:32][OH:33]>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:21]([O:33][CH2:32][CH2:31][CH2:30][Br:29])=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 123083-Bromo-1-propanolHCID 24386Thionyl ChlorideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

生成物 1

HCID 32742783-bromopropyl Methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

A solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine (107 g, 0.32 mol) in CH2Cl2 (520 mL) and DMF (100 mL) was cooled to 0° C. and thionyl chloride (28 mL, 0.39 mol) slowly added. The mixture was stirred at room temperature for 1 hour, then cooled to 5° C. Distilled 3-bromopropanol (35 mL, 3.9 mol) was slowly added, and the solution stirred for 1 hour at room temperature. The solution was then washed with water and the organic layer dried over sodium sulfate and evaporated under reduced pressure. The product was recrystallized from ethyl acetate to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine (12, mp=146° C.).

後処理

  1. temperaturecooled to 5° C
  2. stirringthe solution stirred for 1 hour at room temperature
  3. washThe solution was then washed with water
  4. dry with materialthe organic layer dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe product was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-456b9033347340a1acbd3539a4ba158d
出典データセット
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04761420

反応ノート

読み込み中…

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