Reaction equation
[CH2:1]([N:5]1[C:12](=[O:13])[CH:11]2[C:14]([CH3:16])([CH3:15])[CH:7]([C:8](=[O:18])[NH:9][C:10]2=[O:17])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:28]=1[CH2:29]Cl>CN(C)C=O>[CH2:1]([N:5]1[C:6](=[O:19])[CH:7]2[C:14]([CH3:15])([CH3:16])[CH:11]([C:10](=[O:17])[N:9]([CH2:29][C:28]3[CH:31]=[C:32]([CH3:35])[CH:33]=[CH:34][C:27]=3[CH3:26])[C:8]2=[O:18])[C:12]1=[O:13])[CH2:2][CH2:3][CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
2.6 g of 3-butyl-9,9-dimethyl-2,4,6, 8-tetraoxo-3,7-diazabicyclo[3,3,1]nonane were heated to 120° C. in 50 ml of dimethyl formamide with 1.7 g potassium carbonate for one hour. After cooling, a solution of 1.8 g of 2,5-dimethylbenzyl chloride in 20 ml of dimethyl formamide was added dropwise to the reaction mixture, and the reaction mixture was heated to 120° C. for another 3 hours. The reaction mixture was worked up by distilling off the dimethyl formamide, taking up the residue in dichloromethane, and washing with water adjusted to an alkaline pH value. The dichloromethane phase was separated, dried over magnesium sulfate, and concentrated. After recrystallizing the remaining crude product residue from ether/acetone, 1.2 g of 3-butyl-7-(2,5-dimethylbenzyl)-9, 9-dimethyl-2,4,6,8-tetraoxo-3,7diazabicyclo[3,3, 1]nonane was obtained having a melting point of 159-161° C.
Workup
- temperatureAfter cooling
- distillationby distilling off the dimethyl formamide
- washwashing with water
- customThe dichloromethane phase was separated
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customAfter recrystallizing the remaining crude product residue from ether/acetone
Sources & evidence
- ORD record
- ord-bccb56bf66324b898297c0bd947294be
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05164401
Linked notes
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