Ethylenediamine → 4-(2-Imidazolin-2-YL)-6-methoxy-7-methylchromane

HRID 499025Notes

Reaction equation

HRID 499025 reaction equation
[CH3:1][O:2][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(O)(=O)=[O:27])=CC=1>>[NH:19]1[CH2:16][CH2:17][N:14]=[C:13]1[CH:10]1[C:11]2[C:6](=[CH:5][C:4]([CH3:15])=[C:3]([O:2][CH3:1])[CH:12]=2)[O:27][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 675308144-(2-Imidazolin-2-YL)-6-methoxy-7-methylchromane

Procedure

This compound was prepared in a manner analogous to that of Step G of Example 1, by the reaction of 0.5 gram (0.002 mole) of 7-methyl-6-methoxychromane-4-carbonitrile (iv) and 2 grams (0.008 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 basic alumina (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 0.30 gram 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 basic alumina (3% water)
  3. additiona 99:1 mixture of methylene chloride and methanol
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9e1bc92c52940d3baaca8faa7c83c20
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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