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

HRID 499019Notes

Reaction equation

HRID 499019 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(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])=[CH:3][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 675308994-(2-Imidazolin-2-YL)-7-methylchromane

Procedure

This compound was prepared in a manner analogous to that of Step G of Example 1, by the reaction of 0.6 gram (0.003 mole) of 7-methylchromane-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 mixtures of methylene chloride and methanol as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 0.25 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. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43fc559c00264666b1228adeb298978e
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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