4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide → 4-Hydroxy-N,N,2-trimethyl-1-((4-methylphenyl)sulfonyl)-1H-benzimidazole-6-carboxamide

HRID 1258469Notes

Reaction equation

HRID 1258469 reaction equation
C([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:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH:10]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[OH:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=[C:11]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH:10]=1

Participants

4

Reactant 1

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

Product 1

HCID 672203154-Hydroxy-N,N,2-trimethyl-1-((4-methylphenyl)sulfonyl)-1H-benzimidazole-6-carboxamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(benzyloxy)-N,N,2-trimethyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole-6-carboxamide (29.0 g, 62.6 mmol, Step 3) and 10% palladium on carbon (6.0 g) in tetrahydrofuran (200 mL) was stirred under hydrogen gas (1 atm) at room temperature for 24 hours. Another 4.0 g of 10% palladium on carbon was added, and the mixture was stirred under hydrogen gas (1 atm) at room temperature for additional 6 hours. The resulted mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to afford the title compound as a white solid (23.0 g, 98%).

Workup

  1. stirringthe mixture was stirred under hydrogen gas (1 atm) at room temperature for additional 6 hours
  2. filtrationThe resulted mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ace5895c26d843b0acbcf9c318fba3b3
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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