p-Toluenesulfonic acid → 2,3-Dihydroperimidine

HRID 274155

反応式

HRID 274155 の反応式
C[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.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.CCOCC>[NH:2]1[C:3]2=[C:12]3[C:7](=[CH:6][CH:5]=[CH:4]2)[CH:8]=[CH:9][CH:10]=[C:11]3[NH:13][CH2:14]1

参加物

5

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 140748N,N'-Dimethyl-1,8-naphthalenediamine

生成物 1

HCID 124409652,3-Dihydroperimidine収率 170.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The above aldehyde (1.47 g, 4 mmol) was treated with N,N'-dimethyl-1,8-diaminonaphthalene (4.2 mmol), and para-toluenesulfonic acid (5 mg) in tetrahydrofuran (15 mL) for 20 min at room temperature. The solution was diluted with ether, washed with dilute sodium carbonate, and concentrated. The residue was recrystallized from hexane-ethyl acetate to give the 2,3-dihydroperimidine 7 (1.22 g, 59%): mp 89-90° C.; NMR 7.5-6.75(m, 12H), 6.34(d, 2H), 4.24(t, 1H), 3.9(2t, 4H), 3.02(s, 6H), 1.8-1.2(m, 16H), 0.85(t, 3H).

後処理

  1. washwashed with dilute sodium carbonate
  2. concentrationconcentrated
  3. customThe residue was recrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-fe932fcba30047168c5dd8664105fc6e
出典データセット
uspto-grants-1995_02
特許番号
US05389285

関連ノート

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