4-(3-(2,3-dichlorobenzyl)-2-methyl-7-nitro-3H-benzo[d]imidazol-5-yl)morpholine → 1-[(2,3-dichlorophenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazol-4-amine

HRID 44480Notes

Reaction equation

HRID 44480 reaction equation
[Cl:1][C:2]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=[C:13]([N+:14]([O-])=[O:15])[C:8]=2[N:7]=[C:6]1[CH3:23]>C(O)C.O.[Fe]>[NH3:5].[OH2:15].[Cl:1][C:2]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[CH:12]=[C:13]([NH2:14])[C:8]=2[N:7]=[C:6]1[CH3:23]

Participants

6

Reactant 1

HCID 669766714-(3-(2,3-dichlorobenzyl)-2-methyl-7-nitro-3H-benzo[d]imidazol-5-yl)morpholine

Product 2

HCID 12896473Azane;hydrateHCID 669769571-[(2,3-dichlorophenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazol-4-amineYield 140.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(3-(2,3-dichlorobenzyl)-2-methyl-7-nitro-3H-benzo[d]imidazol-5-yl)morpholine (210 mg), iron powder (56 mg) and FeSO4 (152 mg) in ethanol (25 mL) and H2O (25 mL) was stirred at reflux temperature for 3 h. When TLC showed consumption of all starting material, the mixture was cooled to room temperature and filtered. The filtrate was concentrated in-vacuo and the residue was then purified by silica gel chromatography eluted with MeOH:DCM:NH3.H2O=1:60:0.5% to afford the desired product as a yellow solid (137 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.32 (s, 1H), 2.94 (t, 4H, J=4.8 Hz), 3.68 (t, 4H, J=4.8 Hz), 5.16 (br, s, 2H), 5.40 (s, 2H), 6.09 (d, 1H, J=1.8 Hz), 6.13 (d, 1H, J=1.8 Hz), 6.32 (dd, 1H, J=1.5, 7.5 Hz), 7.25 (t, 1H, J=7.5 Hz), 7.58 (dd, 1H, J=1.5, 7.5 Hz); LC-MS: m/e=391 [M+1]+.

Workup

  1. temperatureat reflux temperature for 3 h
  2. customconsumption of all starting material
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in-vacuo
  5. customthe residue was then purified by silica gel chromatography
  6. washeluted with MeOH

Sources & evidence

ORD record
ord-4f81a0037e1a42039c951bfff1fa199f
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Reaction notes

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