N-methyl-2-pyrrolidone → HCID 58012329, compound

HRID 1698589Notes

Reaction equation

HRID 1698589 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]([C:12]#[N: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>C(=O)([O-])O.[Na+]>[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]([C:12]#[N:13])[C:4]=3[N:3]=2)=[C:22]([O:28][CH3:29])[CH:21]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 67272349HCID 67272349, compound

Product 1

HCID 58012329HCID 58012329, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carbonitrile (1.00 g, 3.82 mmol), 4-chloro-2-methoxy-6-methylaniline (1.97 g, 11.50 mmol) and 1-methyl-2-pyrrolidone (0.5 ml) was heated at 130° C. for 48 h. After cooling, the reaction mixture was diluted with aqueous saturated sodium hydrogen carbonate. The mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as a white powder (670 mg, 44%).

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-67425138cce34d3aa125a16c2d43e8f8
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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