Formic Acid → HCID 178430967, compound

HRID 2260722Notes

Reaction equation

HRID 2260722 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].[CH:13](O)=O.[OH-].[NH4+]>O>[CH3:12][C:3]1[C:2]2[NH:1][CH:13]=[N:8][C:7]=2[CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14923Ammonium HydroxideHCID 158959483-Methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 178430967HCID 178430967, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,3-diamino-6-nitrotoluene (11.81 g), formic acid (88%, 390 mL) and 12N HCI (38 mL) is heated to reflux for 1 hour. The resulting mixture is cooled to room temperature and rotary evaporated. The residue is diluted with water (200 mL), then basified with ammonium hydroxide (28-30%). The suspension is extracted with ethyl acetate (3×200 mL). The combined extracts are dried over magnesium sulfate (MgSO4) and evaporated to afford 4-methyl-5-nitrobenzimidazole as an orange solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 hour
  3. extractionThe suspension is extracted with ethyl acetate (3×200 mL)
  4. dry with materialThe combined extracts are dried over magnesium sulfate (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-454d964f8b5a45baa64d9ab06ecf09b7
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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