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

HRID 1259514Notes

Reaction equation

HRID 1259514 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 (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, MH+=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, quint.).

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-ed8f5cf7520c4a11a73caaeaba239af8
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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