Acetic Acid → HCID 178432210, compound

HRID 1019085Notes

Reaction equation

HRID 1019085 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].Cl.[OH-].[NH4+].[C:16](O)(=O)[CH3:17]>>[CH3:16][C:17]1[NH:1][C:2]2[C:3]([CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 158959483-Methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 178432210HCID 178432210, compound

Procedure

A mixture of 2,3-diamino-6-nitrotoluene (0.945 g, 5.65 mmol), conc. hydrochloric acid (5 mL) and glacial acetic acid (30 mL) is heated to reflux for 2 hours. The mixture is cooled to room temperature, then poured in a mixture of crushed ice (100 mL) and ammonium hydroxide (100 mL) and extracted with 20% methanol in chloroform (2×400 mL). The combined extracts are dried over potassium carbonate and rotary evaporated to afford 2,4-dimethyl-5-nitrobenzimidazole as a brown solid. The product is used in the following step without further purification.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with 20% methanol in chloroform (2×400 mL)
  4. dry with materialThe combined extracts are dried over potassium carbonate
  5. customrotary evaporated

Sources & evidence

ORD record
ord-4e69ea512c294b00a1650e7cef5aae32
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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