Sodium Hydroxide → 1-Chloro-2,2,5,5-tetramethylimidazolidin-4-one
Reaction equation
[CH3:1][C:2]1([CH3:10])[NH:6][C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[NH:3]1.[OH-].[Na+].[Cl:13]Cl.[K+].[Br-]>>[Cl:13][N:3]1[C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[NH:6][C:2]1([CH3:10])[CH3:1]Participants
Procedure
14.2 Grams (0.1 mole) of 2,2,5,5-tetramethylimidazolidin-4-one prepared as in example 2 was dissolved in 100 milliliters of 1 Normal sodium hydroxide solution (0.1 mole) in a 250 milliliter flask. The flask containing the mixture was placed in an ice bath and maintained at or below 10° C. with stirring while chlorine gas was bubbled in until the pH reached 7.0. The product 1-chloro-2,2,5,5-tetramethylimidazolidin-4-one which precipitated as a white solid was recovered by suction filtration and was purified by recrystallization from an ether/hexane mixture. The product yield was 17.7 grams or 95% of that theoretically expected. The product had a melting point range of 157.0°-157.5° C. Analysis of the product by proton NMR and IR spectroscopy yielded the following results: 1H NMR (CDCl3) δ=1.32 (S,6H), δ=1.46 (S,6H), δ=7.57 (Broad,1H); IR (KBr) 1670, 1720, 3160 cm-1.
Workup
- additionThe flask containing the mixture
- customwas placed in an ice bath
- temperaturemaintained at or below 10° C.
- customwas bubbled in until the pH
- customThe product 1-chloro-2,2,5,5-tetramethylimidazolidin-4-one which precipitated as a white solid
- filtrationwas recovered by suction filtration
- customwas purified by recrystallization from an ether/hexane mixture
- customa melting point range of 157.0°-157.5° C
- customAnalysis of the product by proton NMR and IR spectroscopy yielded the
- customfollowing results
Sources & evidence
- ORD record
- ord-127a33cd8a0341258808fd0cfdd599b8
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05057612
Reaction notes
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