Formic Acid → HCID 69357050, compound

HRID 852602Notes

Reaction equation

HRID 852602 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:15][CH2:16][CH3:17].[CH:18](O)=O>CCOC(C)=O>[CH2:16]([N:15]1[C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=2[N:1]=[CH:18]1)[CH3:17]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 69356918HCID 69356918, compound

Product 1

HCID 69357050HCID 69357050, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-amino-3-(ethylamino)-5-nitrobenzoate (D205) (850 mg, 3.55 mmol, 1 equiv) was dissolved in formic acid (20 ml) and the resulting solution was stirred at 100° C. for 45 min then cooled to room temperature and diluted with AcOEt (200 ml). The organic phase was washed with a 2N aqueous NaOH solution, dried over MgSO4 and concentrated in vacuo to give methyl 1-ethyl-4-nitro-1H-benzimidazole-6-carboxylate (D206) (700 mg, 79%) as a tan solid which was used in the next step without further purification. [M+H]+=250.1, RT=2.41 min.

Workup

  1. temperaturethen cooled to room temperature
  2. washThe organic phase was washed with a 2N aqueous NaOH solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b9e42b3d54d4159a03415b37dafe676
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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