2-Methyl-4-methoxyaniline → HCID 57786358, compound

HRID 1399285Notes

Reaction equation

HRID 1399285 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8](Cl)[N:7]([CH2:12][CH2:13][CH2:14]Cl)[C:6]=2[C:5]([C:16]([O:18][CH3:19])=[O:17])=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24]([CH3:29])[CH:23]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC1C=CC=CC=1C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]([O:18][CH3:19])=[O:17])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:26]([C:25]3[CH:27]=[CH:28][C:22]([O:21][CH3:20])=[CH:23][C:24]=3[CH3:29])[CH2:14][CH2:13][CH2:12][N:7]21

Participants

6

Reactant 3

HCID 76102-Methyl-4-methoxyanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 68765133HCID 68765133, compound

Product 1

HCID 57786358HCID 57786358, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-bromo-2-chloro-1-(3-chloropropyl)-1H-benzimidazole-7-carboxylate (429 mg, 1.17 mmol), 4-methoxy-2-methylaniline (0.301 mL, 2.34 mmol) and p-toluenesulfonic acid monohydrate (0.0223, 0.117 mmol) in o-xylene (2.4 mL) was stirred at 120° C. for 3 days, and diluted with aqueous sodium bicarbonate. The resultant mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on NH silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a brown solid (301 mg, 0.700 mmol, 60%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on NH silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-7ce4285a774b4cc7a0f8756c59986572
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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