Ammonia → HCID 58190839, compound

HRID 1844959Notes

Reaction equation

HRID 1844959 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[NH:12][C:11]([NH2:14])=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[N+:15]([O-])([O-:17])=[O:16].[K+].N>OS(O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH2:14])[NH:10][C:9]=2[CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 178497585HCID 178497585, compound

Product 1

HCID 58190839HCID 58190839, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-30 °C

Procedure

1.0 g (5.2 mmol) of 2-amino-3H-benzoimidazole-4-carboxylic acid methyl ester was suspended in 10 mL of conc. H2SO4 at −15° C. and cooled to −30° C. Potassium nitrate (0.58 g, 5.72 mmol) dissolved in 10 mL of sulfuric acid and cooled to 0° C. was then added dropwise to the reaction mixture. The reaction mixture was stirred −30° C. for 15 min then warmed to −10° C. over 30 min. Then the mixture was poured into a beaker containing ice and neutralized (˜pH=8) with concentrated aqueous ammonia solution. The resulting solid was filtered. The solid obtained was washed with cold water and ether, and dried under vacuum to provide 0.85 g (70%) 2-amino-6-nitro-1H-benzoimidazole-4-carboxylic acid methyl ester as a solid. LCMS: 239 (M+1)+.

Workup

  1. temperaturecooled to 0° C.
  2. additionwas then added dropwise to the reaction mixture
  3. temperaturethen warmed to −10° C. over 30 min
  4. additionThen the mixture was poured into a beaker
  5. filtrationThe resulting solid was filtered
  6. customThe solid obtained
  7. washwas washed with cold water and ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9345ef1a94b44f4a8fbd5bbfcb12fc26
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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