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

HRID 1698562
Notes
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Reaction equation

HRID 1698562 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:4]=2[N:3]=1.[Cl:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH2:24])=[C:22]([O:28][CH3:29])[CH:21]=1.CN1CCCC1=O>O>[Cl:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH:24][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:4]=3[N:3]=2)=[C:22]([O:28][CH3:29])[CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 672730962-Chloro-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole

Product 1

HCID 58012305N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazol-2-amineYield 55.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-chloro-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole (120 mg, 0.450 mmol), 4-chloro-2-methoxy-6-methylaniline (231 mg, 1.35 mmol) and 1-methyl-2-pyrrolidone (0.5 mL) was stirred at 130° C. for 2 days under nitrogen atmosphere. The mixture was diluted with water, extracted with ethyl acetate and 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 (100 mg, 55%).

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-c137ad9cd4474bf4940b40f6dea8cc5f
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