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Dimethylamine tetrahydrofuran → 4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide

HRID 1258468
Notes
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Reaction equation

HRID 1258468 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:30]1[CH2:34]CCC1.[CH3:35][NH:36][CH3:37]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=[C:11]([C:34]([N:36]([CH3:37])[CH3:35])=[O:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 22320367Dimethylamine tetrahydrofuranHCID 67219535HCID 67219535, compound

Product 1

HCID 672201744-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamideYield 42%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(benzyloxy)-6-bromo-2-methyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole (53.0 g, 112 mmol, Step 2) and tetrakis(triphenylphosphine)palladium (25.9 g, 22.4 mmol) in 2 mol/L dimethylamine tetrahydrofuran solution (580 mL) was stirred at 65° C. under carbon monoxide gas (1 atm) for 32 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate. The organic mixture was washed with saturated ammonium chloride aqueous solution and brine, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:2 to 1:3) to afford the title compound as a white solid (21.8 g, 42%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic mixture was washed with saturated ammonium chloride aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:2 to 1:3)

Sources & evidence

ORD record
ord-3582d38ded2440489fe358c7274c10ea
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466166B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes