Ethylenediamine → 4-(2-IMIDAZOLIN-2YL)-7-METHYL-2H,3H,4H-BENZO[e]THIIN

Reaction equation

CO[C:3]1[CH:12]=[C:11]2[C:6](C[CH2:8][CH2:9][CH:10]2[C:13]#[N:14])=[CH:5][C:4]=1[CH3:15].[CH2:16]([NH2:19])[CH2:17]N.C1(C)C=CC([S:26](O)(=O)=O)=CC=1>>[NH:19]1[CH2:16][CH2:17][N:14]=[C:13]1[CH:10]1[C:11]2[CH:12]=[CH:3][C:4]([CH3:15])=[CH:5][C:6]=2[S:26][CH2:8][CH2:9]1

Participants

Reactant 3

HCID 3301Ethylenediamine

HCID 6101p-Toluenesulfonic acid

HCID 675300557-Methoxy-6-methyl-1,2,3,4-tetrahydronaphthalenecarbonitrile

Product 1

HCID 675299204-(2-IMIDAZOLIN-2YL)-7-METHYL-2H,3H,4H-BENZO[e]THIIN

Procedure

This compound was prepared in a manner analogous to that of Step G of Example 1, by the reaction of 2.0 grams (0.0106 mole) of 7-methyl-2H,3H,4H-benzo[e]thiin-4-carbonitrile (iv) and 6 grams (0.024 mole) of the ethylenediamine salt of p-toluenesulfonic acid (prepared in Step F of Example 1). The reaction product was purified by column chromatography on Grade II alumina (basic-3% water) using a 99:1 mixture of methylene chloride and methanol, respectively, as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 1.2 grams of subject compound. The NMR spectrum was consistent with the proposed structure.