Imidazole → 1-(diethoxymethyl)-1H-imidazole
Reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:18](OCC)([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>>[CH2:20]([O:19][CH:18]([O:22][CH2:23][CH3:24])[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH3:21]Participants
4
Procedure
The procedure of Curtis and Brown was followed: Imidazole (204 g, 3.0M), triethyl orthoformate (1300 ml), and p-toluenesulfonic acid monohydrate (3.0 g) were placed in a 2-liter round bottom with a stirring bar and fitted with a Penn-State distillation head. The reaction was heated at reflux and ethanol removed by distillation. Heating was continued until the reaction temperature rose above 140° C. (ca. 2.5 hours). The reaction was cooled to room temperature and potassium carbonate was added to neutralize the acid catalyst. The desired product was isolated by distillation under vacuum, bp 105° C. (5 mm) after collecting a forerun below 105° C.
Workup
- customfitted with a Penn-State distillation head
- temperatureThe reaction was heated
- temperatureat reflux
- customethanol removed by distillation
- temperatureHeating
- customrose above 140° C.
- custom(ca. 2.5 hours)
- additionpotassium carbonate was added
Sources & evidence
- ORD record
- ord-381fff847fc74e47b967f9c6890fc861
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05147863
Reaction notes
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