Ethylenediamine → 6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxy-3-(3-morpholin-4-ylpropoxy)aniline

HRID 536230Notes

Reaction equation

HRID 536230 reaction equation
[NH2:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:22](N)[CH2:23][NH2:24].[S]>O>[NH:5]1[CH2:22][CH2:23][N:24]=[C:4]1[C:3]1[C:2]([NH2:1])=[C:9]([O:10][CH3:11])[C:8]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 582198372-Amino-3-methoxy-4-(3-morpholin-4-ylpropoxy)benzonitrile

Product 1

HCID 582198516-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxy-3-(3-morpholin-4-ylpropoxy)anilineYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a degassed mixture of 2-amino-3-methoxy-4-(3-morpholin-4-ylpropoxy)benzonitrile (Step 3, 6.5 g, 22.2 mmol) and ethylene diamine (40 mL) was added sulfur (1.8 g, 55.4 mmol). The mixture was stirred at 100° C. for 3 h at which time water was added to the reaction mixture. The precipitate that was formed was collected and washed with water and then dried overnight under vacuum to provide the title compound (3.2 g, 43%): HPLC MS RT=1.25 min, MW=335.2; 1H NMR (DMSO-d6) δ: 7.15 (1H, d), 6.86 (2H, br s), 6.25 (1H, d), 4.02 (2H, t), 3.66 (3H, s), 3.57 (8H, m), 2.46 (2H, t), 2.44 (4H, m), 1.89 (2H, m).

Workup

  1. additionwas added to the reaction mixture
  2. customThe precipitate that was formed
  3. customwas collected
  4. washwashed with water
  5. customdried overnight under vacuum

Sources & evidence

ORD record
ord-238739429a8d4620b7c264216f624ab9
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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