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

HRID 2220185Notes

Reaction equation

HRID 2220185 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

4

Reactant 3

HCID 3301EthylenediamineHCID 6101p-Toluenesulfonic acidHCID 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.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step G of Example 1
  2. customThe reaction product was purified by column chromatography on Grade II alumina (basic-3% water)
  3. additiona 99:1 mixture of methylene chloride and methanol
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b515637c508e421baa5d6a8b009a680f
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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