Water → 5-(2-Hydroxy-4-nitroanilinocarbonyl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74216

Reaction equation

HRID 74216 reaction equation
Cl.[CH3:2][C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:6]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:5]=2[N:4]=1.S(Cl)(Cl)=O.O[C:26]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:27]=1N.C([N:38](CC)CC)C.[OH2:43]>C1(C)C=CC=CC=1.CN(C=O)C.O1CCCC1>[OH:43][C:27]1[CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=[CH:32][C:26]=1[NH:38][C:18]([C:16]1[CH:15]=[CH:14][C:6]2[N:7]([CH:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[C:3]([CH3:2])=[N:4][C:5]=2[CH:17]=1)=[O:20]

Participants

9

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 36133892-Amino-4-NitrophenolHCID 674984452-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

Product 1

HCID 674981775-(2-Hydroxy-4-nitroanilinocarbonyl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazoleYield 17.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) (0.75 g, 2.9 mmol) in toluene (10 mL) containing DMF (1 drop) was added thionyl chloride (0.41 g, 3.4 mmol), and this was refluxed for 7 hours with stirring. After the reaction was complete, concentration at reduced pressure gave a residue that was added to 2-hydroxy-5-nitroaniline (0.44 g, 2.9 mmol), triethylamine (0.32 g, 3.2 mmol) and tetrahydrofuran (5 mL), and this was stirred at room temperature for 3 hours. After the reaction was complete, water (30 mL) was added and the precipitated crystals were filtered off. After the crystals were washed with water, they were dried with heating at reduced pressure to yield the title compound (195 mg, 17.1%) as a light brown solid.

Workup

  1. temperaturethis was refluxed for 7 hours
  2. concentrationconcentration at reduced pressure
  3. customgave a residue that
  4. stirringthis was stirred at room temperature for 3 hours
  5. filtrationthe precipitated crystals were filtered off
  6. washAfter the crystals were washed with water, they
  7. customwere dried
  8. temperaturewith heating at reduced pressure

Sources & evidence

ORD record
ord-0d156a25ad514904a3cdcd09accb1945
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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