Triethylamine → 4-Methylbenzimidazole

HRID 1492484Notes

Reaction equation

HRID 1492484 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-Methylbenzimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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° 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 of the title A compound as a brown solid that was used in the next reaction without purification.

Workup

  1. temperatureThe mixture was cooled to 0°
  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-a7afdf562c564f9e9b3a0e548b24b2af
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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