p-Toluenesulfonic acid → 2,3-Dihydroperimidine

HRID 274155Notes

Reaction equation

HRID 274155 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 124409652,3-DihydroperimidineYield 170.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-fe932fcba30047168c5dd8664105fc6e
Source dataset
uspto-grants-1995_02
Patent number
US05389285

Reaction notes

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