Formic Acid → HCID 69356779, compound

HRID 852619Notes

Reaction equation

HRID 852619 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[CH:16](O)=O>>[N+:13]([C:10]1[C:11]2[N:12]=[CH:16][NH:1][C:2]=2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 69356421HCID 69356421, compound

Product 1

HCID 69356779HCID 69356779, compoundYield 110%

Procedure

A solution of methyl 3,4-diamino-5-nitrobenzoate (D245) (1.3 g, 6.16 mmol, 1 equiv) in HCOOH (20 ml) was stirred at 100° C. for 1 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and a 2N aqueous NaOH solution and the layers were separated. The organic phase was dried over MgSO4 and concentrated in vacuo to give methyl 4-nitro-1H-benzimidazole-6-carboxylate (D250) (1.5 g, 110%) as a light brown solid which was used in the next step without further purification. [M+H]+=222.3, RT=2.29 min.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between AcOEt
  3. customa 2N aqueous NaOH solution and the layers were separated
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ee88085e8634793a055645be680c0a2
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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