Diethyl Ether → HCID 19905727, compound

HRID 2372017Notes

Reaction equation

HRID 2372017 reaction equation
[CH2:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[NH:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=CC=1.C(O[CH2:36][CH3:37])(=O)C.[CH3:38][CH2:39]OCC>>[CH2:17]([N:16]1[C:14]2=[C:15]3[C:10](=[CH:11][CH:12]=[CH:13]2)[CH:9]=[CH:8][CH:7]=[C:6]3[N:5]([CH2:38][CH2:39][CH2:36][CH3:37])[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:31][CH2:21][CH2:26][CH2:25][CH3:24])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 15404097HCID 15404097, compound

Product 1

HCID 19905727HCID 19905727, compound

Procedure

A mixture of N,N'-dibutyl-1,8-naphthalene diamine (prepared in Example 2) (1.35 g, 5 mmol), nonyl aldehyde (0.78 g, 5.5 mmol), p-toluene sulfonic acid (5 mg) and ethyl acetate (5 ml) was prepared and stirred at room temperature for 15 minutes. More nonyl aldehyde (0.16 g, 1.1 mmol) was added to complete the reaction. The mixture was diluted with ether (50 ml), washed with saturated sodium carbonate (10 ml), washed with water and brine, and dried over potassium carbonate. The extract was concentrated to an oil that would not crystallize from ethyl acetate-hexane. The oil was dried under vacuumn to give crude 2,3-dihydro-1,3-dibutyl-2-octyl perimidine: NMR (CDCl3) 7.05(m, 4H), 6.35(d, 2H), 4.10(t, 1H), 3.5 and 3.0(m, 4H), 1.8-1.0(m, 20H), 0.9(t, 9H).

Workup

  1. customwas prepared
  2. customthe reaction
  3. washwashed with saturated sodium carbonate (10 ml)
  4. washwashed with water and brine
  5. dry with materialdried over potassium carbonate
  6. concentrationThe extract was concentrated to an oil that would not
  7. customcrystallize from ethyl acetate-hexane
  8. customThe oil was dried under vacuumn

Sources & evidence

ORD record
ord-140c1e2d036a4893b6f76b391cb84f7f
Source dataset
uspto-grants-1992_03
Patent number
US05097029

Reaction notes

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