Methane → HCID 45789404, compound

HRID 969513Notes

Reaction equation

HRID 969513 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.C.O.NN.CCCCCCC>CO.[Fe](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 8900HeptaneHCID 24654Hydrazine hydrate (1:1)HCID 69135260HCID 69135260, compound

Product 1

HCID 45789404HCID 45789404, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 19 g (70 mmol) 6-bromo-1,2-dimethyl-4-nitro-1H-benzimidazole in 250 ml methanol were added 13.7 g (84 mmol) iron(III) chloride and 6 g activated charcoal. The reaction mixture was heated to 80° C. and 17 ml hydrazine hydrate (95%) were slowly added. After refluxing for 3 h, the hot reaction mixture was filtered through celite and the precipitate was washed with methanol and dichloromethane. The filtrate was evaporated to give a suspension, which was treated with n-heptane. The precipitate was collected, washed with n-heptane and dried in vacuo to give 13.3 g (79%) of the title compound as a white solid. m.p. 206-209° C.

Workup

  1. temperatureAfter refluxing for 3 h
  2. filtrationthe hot reaction mixture was filtered through celite
  3. washthe precipitate was washed with methanol and dichloromethane
  4. customThe filtrate was evaporated
  5. customto give a suspension, which
  6. customThe precipitate was collected
  7. washwashed with n-heptane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d5663e43362d43889408e5f1ce22a0ed
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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