p-Toluenesulfonic acid → 2,3-Dihydroperimidine

HRID 274155

반응식

HRID 274155 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 124409652,3-Dihydroperimidine수율 170.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fe932fcba30047168c5dd8664105fc6e
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389285

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