Triethylamine → 4-Methylbenzimidazole
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureto warm to room temperature
- customthe reaction was quenched with sodium bicarbonate
- extractionThe aqueous phase was extracted with ethyl acetate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customthe solvent removed
Sources & evidence
- ORD record
- ord-db7a59d5b616435bbb5f75d38b4a5975
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212177
Reaction notes
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