HCID 178450789, compound → HCID 178450788, compound

HRID 1874837Notes

Reaction equation

HRID 1874837 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:10][C:6]=2[CH:5]=1)([O-])=O>C(O)C.[Pt](=O)=O>[NH2:1][C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[N:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 178450789HCID 178450789, compound

Product 1

HCID 178450788HCID 178450788, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Platinum(IV) oxide (0.020 g, 0.090 mmol) was added to a suspension of 1,1-dimethylethyl 5-nitro-1H-benzimidazole-2-carboxylate (0.472 g, 1.793 mmol) in ethanol (20 mL) in a pressure vessel. The mixture was evacuated and flushed with nitrogen, then evacuated and flushed with hydrogen (50 Psi). After 1 h, the reaction mixture was filtered through Celite. The filtrate was concentrated and the residue was dried under vacuum to give the title compound (0.359 g, 69%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 10.03 (s, 1H), 7.66 (d, 1H), 6.49-6.90 (m, 2H), 3.77 (br. s., 2H), 1.64 (s, 9H). MS: m/z 234 (M+1).

Workup

  1. customThe mixture was evacuated
  2. customflushed with nitrogen
  3. customevacuated
  4. customflushed with hydrogen (50 Psi)
  5. filtrationthe reaction mixture was filtered through Celite
  6. concentrationThe filtrate was concentrated
  7. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-5ec05c89c93d4934a0d41f33cce3e918
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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