Sulfuric Acid → HCID 136403421, compound
Reaction equation
[CH:1]([O-:5])([O-])[O:2][CH3:3].[CH3:6]N1CCN(C)C1=O.S(=O)(=O)(O)O.[N+:19]([N:22]=[C:23]1[NH:28][CH2:27][CH2:26][CH2:25][NH:24]1)([O-:21])=[O:20]>>[CH3:6][O:5][CH:1]([O:2][CH3:3])[N:24]1[CH2:25][CH2:26][CH2:27][NH:28][C:23]1=[N:22][N+:19]([O-:21])=[O:20]Participants
Procedure
20.0 g of methyl orthoformate was dropped in about 1.5 hours in a mixture of 10 g of 2-nitroiminohexahydropyrimidine, 20 ml of 1,3-dimethyl-2-imidazolidinone and 0.05 g of sulfuric acid at 150° C., followed by heating under reflux for further 1 hour while removing the resultant distillate by means of the Dean-Stark trap. After cooling to room temperature, the mixture was poured into water, and extracted with ethyl acetate. After washing with water, the extract was dried with anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The resultant oily substance was purified by column chromatography [silica gel, eluant: hexane/ethyl acetate (1:2)] to give 1.5 g of 1-dimethoxymethyl-2-nitroiminohexahydropyrimidine.
Workup
- temperatureby heating
- temperatureunder reflux for further 1 hour
- customwhile removing the resultant distillate by means of the Dean-Stark trap
- additionthe mixture was poured into water
- extractionextracted with ethyl acetate
- washAfter washing with water
- dry with materialthe extract was dried with anhydrous magnesium sulfate
- distillationafter which the solvent was distilled off under reduced pressure
- customThe resultant oily substance was purified by column chromatography [silica gel, eluant: hexane/ethyl acetate (1:2)]
Sources & evidence
- ORD record
- ord-563d7e93a7d145ac8691b969ca943b54
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05192778
Reaction notes
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