p-Toluenesulfonic acid monohydrate → N5-[4-Chloro-7-(1-ethylpropyl)-1-prop-2-en-1-yl-1H-benzimidazol-2-yl]-N2,N2,4-trimethylpyridine-2,5-diamine

HRID 1398814Notes

Reaction equation

HRID 1398814 reaction equation
[CH2:1]([N:4]1[C:8]2[C:9]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:10][CH:11]=[C:12]([Cl:13])[C:7]=2[N:6]=[C:5]1Cl)[CH:2]=[CH2:3].[CH3:20][N:21]([CH3:30])[C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([NH2:29])=[CH:24][N:23]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN1CCCC1=O.C(OCC)(=O)C>[Cl:13][C:12]1[C:7]2[N:6]=[C:5]([NH:29][C:25]3[C:26]([CH3:28])=[CH:27][C:22]([N:21]([CH3:30])[CH3:20])=[N:23][CH:24]=3)[N:4]([CH2:1][CH:2]=[CH2:3])[C:8]=2[C:9]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22136281N2,N2,4-trimethylpyridine-2,5-diamineHCID 687711711-Allyl-2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazole

Product 1

HCID 68773733N5-[4-Chloro-7-(1-ethylpropyl)-1-prop-2-en-1-yl-1H-benzimidazol-2-yl]-N2,N2,4-trimethylpyridine-2,5-diamineYield 26%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1-allyl-2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazole (1.19 g, 4.00 mmol), N2,N2,4-trimethylpyridine-2,5-diamine (1.21 g, 8.00 mmol) and p-toluenesulfonic acid monohydrate (760 mg, 4.00 mmol) in 1-methyl-2-pyrrolidinone (12 mL) was irradiated by microwave at 180° C. for 1 hr. After cooling, the mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 30-80% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound (430 mg, 1.04 mmol, 26%) as a colorless solid.

Workup

  1. customwas irradiated by microwave at 180° C. for 1 hr
  2. temperatureAfter cooling
  3. washwashed with aqueous sodium bicarbonate, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel eluting with a 30-80% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give the solid, which
  9. customwas recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ad1e2a30fa61453696d772b95fff70be
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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