Dimethylformamide → 2-(5-methyl-1H-imidazol-4-yl)ethanol oxalate
Reaction equation
Br[CH:2]1[CH2:6][CH2:5][O:4][C:3]1([CH3:8])[OH:7].C(O)(=[O:11])C.[CH:13]([NH2:15])=[NH:14].C(NCC)C.CN(C)[CH:23]=[O:24]>>[C:23]([OH:24])(=[O:11])[C:3]([OH:7])=[O:4].[CH3:8][C:3]1[NH:15][CH:13]=[N:14][C:2]=1[CH2:6][CH2:5][OH:4]Participants
5
Conditions
- Temperature
- 80 °C
Procedure
5.0 g of 3-bromo-2-methyl-tetrahydrofuran-2-ol and 5.75 g of formamidine acetate were added to 15 ml of N,N-dimethylformamide. 5 g of diethylamine was slowly added to the reaction mixture, which was then stirred for about 4 hours at 80° C. and was distilled in vacuo for about 1 hour at the same temperature. The resulting oily residue was diluted with 25 ml of acetone. 4.95 g of oxalic acid was added to the reaction mixture, which was then stirred for about 1 hour. The resulting solid was filtered and washed with acetone to give 2.5 g of 2-(5-methyl-1H-imidazol-4-yl)ethanol oxalate (yield: 42%).
Workup
- distillationwas distilled in vacuo for about 1 hour at the same temperature
- additionThe resulting oily residue was diluted with 25 ml of acetone
- addition4.95 g of oxalic acid was added to the reaction mixture, which
- stirringwas then stirred for about 1 hour
- filtrationThe resulting solid was filtered
- washwashed with acetone
Sources & evidence
- ORD record
- ord-4f07a90ad4d24bee9af17a0712dbf074
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706888B2
Reaction notes
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