Methyl iodide → HCID 69434910, compound

HRID 888100Notes

Reaction equation

HRID 888100 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[NH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[C:17]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:17][N:8]1[C:7]2[CH:15]=[CH:16][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[N:10]=[C:9]1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178526481HCID 178526481, compound

Product 1

HCID 69434910HCID 69434910, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Nitro-2-(trifluoromethyl)-1H-benzo[d]imidazole (4.45 g, 19.1 mmol, 1.0 eq.), K2CO3 (3.2 g, 23.0 mmol, 1.2 eq.) and methyliodide (1.2 ml, 19.1 mmol, 1.0 eq.) were dissolved in DMF (anhydrous, 50 ml). The reaction was stirred at RT for 2 h. TLC showed mostly starting material. The mixture was stirred at RT for another 16 h. The DMF was removed in vacuo and the residue redissolved in a minimum of hot EtOAc and recrystallized (gave mixture). Crystals and mother liquor were combined and evaporated down. Purification by column chromatography (0-25% EtOAc/Hex) yielded 1-methyl-5-Nitro-2-(trifluoromethyl)-1H-benzo[d]imidazole (1 g) and 1-methyl-6-Nitro-2-(trifluoromethyl)-1H-benzo[d]imidazole. Structures confirmed by NOESY NMR.

Workup

  1. stirringThe mixture was stirred at RT for another 16 h
  2. customThe DMF was removed in vacuo
  3. dissolutionthe residue redissolved in a minimum of hot EtOAc
  4. customrecrystallized
  5. custom(gave mixture)
  6. customevaporated down
  7. customPurification by column chromatography (0-25% EtOAc/Hex)

Sources & evidence

ORD record
ord-dc5a242f3a8b4491b0008f7f3143e9fa
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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