Ethylene Glycol → Diethyl 2-methyl-4-(2-nitrophenyl)-6-ethylenedioxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 894702ノート

反応式

HRID 894702 の反応式
C[C:2]1[NH:3][C:4]([CH:27]=O)=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:29]([OH:32])[CH2:30][OH:31].[C:33]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:27][C:4]1[N:3]2[O:32][CH2:29][CH2:30][O:31][C:2]2=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([CH3:33])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:5]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 13388352Diethyl 2-methyl-4-(2-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate

生成物 1

HCID 70071585Diethyl 2-methyl-4-(2-nitrophenyl)-6-ethylenedioxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of diethyl 2-methyl-4-(2-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (388.37 mg), ethylene glycol (186.21 mg) and p-toluenesulfonic acid (catalytic amount) in absolute benzene (5 ml) was refluxed for 45 minutes under azeotropic dehydration. The reaction mixture was allowed to stand and washed twice with an aqueous solution of sodium bicarbonate. After removal of the solvent, the residue immediately turned into crystals. Thus obtained crystals were recrystallized from a mixture of ethanol and diisopropyl ether to give yellow pure crystals (0.32 g) of diethyl 2-methyl-4-(2-nitrophenyl)-6-ethylenedioxymethyl-1,4-dihydropyridine-3,5-dicarboxylate, m.p. 152° to 153.5° C.

後処理

  1. temperaturewas refluxed for 45 minutes under azeotropic dehydration
  2. washwashed twice with an aqueous solution of sodium bicarbonate
  3. customAfter removal of the solvent
  4. customThus obtained crystals were recrystallized from a mixture of ethanol and diisopropyl ether

出典と根拠

ORDレコード
ord-b63192aa557944c3ba9869d6824af63a
出典データセット
uspto-grants-1981_08
特許番号
US04284634

反応ノート

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