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N-methyl-2-pyrrolidone → N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazol-2-amine

HRID 1698565
Notes
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Reaction equation

HRID 1698565 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11]([CH3:12])[C:4]=2[N:3]=1.[Cl:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:22]([NH2:23])=[C:21]([O:27][CH3:28])[CH:20]=1.CN1CCCC1=O>O>[Cl:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:22]([NH:23][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11]([CH3:12])[C:4]=3[N:3]=2)=[C:21]([O:27][CH3:28])[CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 672727562-Chloro-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazole

Product 1

HCID 11977539N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazol-2-amineYield 34.4%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazole (100 mg, 0.399 mmol), 4-chloro-2-methoxy-6-methylaniline (205 mg, 1.20 mmol) and 1-methyl-2-pyrrolidone (0.2 mL) was stirred at 120° C. for 2 days under nitrogen atmosphere. The mixture was diluted with water and extracted with ethyl acetate, washed with brine. The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1-1:1) and crystallized from iso-propanol to afford the title compound as colorless crystals (53 mg, 34%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1-1:1)
  6. customcrystallized from iso-propanol

Sources & evidence

ORD record
ord-240750d60b23439c8a1565af64a9d86c
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163935B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes