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

HRID 2220182Notes

Reaction equation

HRID 2220182 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-e151067f637a43f7b8ed373f325c0caf
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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