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

HRID 2372015

반응식

HRID 2372015 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ac0b20b73da4f768285e83a2a21e0a9
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05097029

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