Butanal → 2,3-Dihydro-1,3-dimethyl-2-propyl perimidine

HRID 2372015

反応式

HRID 2372015 の反応式
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH3:14])[CH:6]=[CH:5][CH:4]=1.[CH:15](=O)[CH2:16][CH2:17]C.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>O.O1CCCC1>[CH3:14][N:13]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[N:2]([CH3:20])[CH:1]1[CH2:15][CH2:16][CH3:17]

参加物

7

反応物 4

HCID 261ButanalHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 140748N,N'-Dimethyl-1,8-naphthalenediamine

生成物 1

HCID 199057282,3-Dihydro-1,3-dimethyl-2-propyl perimidine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of N,N'-dimethyl-1,8-naphthalene diamine (prepared in Example 1) (0.93 g, 5 mmol), distilled butyraldehyde (0.43 g, 6 mmol), p-toluene sulfonic acid (5 mg), and tetrahydrofuran (5 ml), was stirred at room temperature for 15 minutes. The mixture was basified with 25% sodium hydroxide (1.0 ml), diluted with water (20 ml) and extracted with ethyl ether (100 ml). The extract was dried over potassium carbonate and concentrated to an oil which was recrystallized from ether-hexane to give crystals of 2,3-dihydro-1,3-dimethyl-2-propyl perimidine: mp 70°-71° C.; NMR (CDCl3) 7.08(m, 4H), 6.29(m, 2H), 4.22(t, 1H), 3.03(s, 6H), 1.4(m, 4H), 0.8(t, 3H); IR (KBr) 1592, 1582 cm-1.

後処理

  1. extractionextracted with ethyl ether (100 ml)
  2. dry with materialThe extract was dried over potassium carbonate
  3. concentrationconcentrated to an oil which
  4. customwas recrystallized from ether-hexane

出典と根拠

ORDレコード
ord-0ac0b20b73da4f768285e83a2a21e0a9
出典データセット
uspto-grants-1992_03
特許番号
US05097029

関連ノート

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