Triethylamine → 4-Methylbenzimidazole

HRID 248836

Reaction equation

HRID 248836 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10](N(CC)CC)C.COC(Cl)Cl>O1CCCC1>[CH3:9][C:3]1[C:2]2[N:1]=[CH:10][NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 175932,3-DiaminotolueneHCID 21004Methane, dichloromethoxy-

Product 1

HCID 15193414-MethylbenzimidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2,3 Diaminotoluene (675 mg, 5.53 mmol) was dissolved in 10 mL of dry tetrahydrofuran and triethylamine (0.77 mL, 5.53 mmol) was added. The mixture was cooled to 0° C. and 1,1-dichloromethyl methyl ether (0.50 mL, 5.53 mmol) was added and the reaction was allowed to warm to room temperature. After 20 hours, the reaction was quenched with sodium bicarbonate. The aqueous phase was extracted with ethyl acetate, dried over magnesium sulfate, filtered and the solvent removed to yield 730 mg (100%) of a brown solid.

Workup

  1. temperatureto warm to room temperature
  2. customthe reaction was quenched with sodium bicarbonate
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-db7a59d5b616435bbb5f75d38b4a5975
Source dataset
uspto-grants-1993_05
Patent number
US05212177

Linked notes

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