Sodium Hydroxide → HCID 90314001, compound

HRID 1505774Notes

Reaction equation

HRID 1505774 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[C:11]=2[N:10]=1)#[N:7].[OH-:22].[Na+]>S(=O)(=O)(O)O>[NH2:7][C:6](=[O:22])[CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 90229334HCID 90229334, compound

Product 1

HCID 90314001HCID 90314001, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Under ice-cooling, potassium nitrate (117 mg) was added slowly portion-wise to a stirring solution of methyl 2-(cyanomethyl)-1H-benzimidazole-4-carboxylate (prepared as described in EP1479681) (226 mg) in conc. sulfuric acid (5 mL), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice, and alkalified with 3N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was washed with MeOH, filtered and dried to obtain the titled compound (243 mg).

Workup

  1. temperatureUnder ice-cooling
  2. additionThe reaction mixture was poured into ice
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. washThe residue was washed with MeOH
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-bb76e03e32f141ee9338c2c232c5eaa3
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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