Water → HCID 19779488, compound
Reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][O+](C)C.[CH2:10]([N:12]([CH2:28][CH3:29])[CH2:13][CH2:14][CH2:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)(=[NH:18])=[O:17])[CH3:11].O.[OH-].[Na+]>C(Cl)Cl>[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:28]([N+:12]([CH2:10][CH3:11])([CH3:6])[CH2:13][CH2:14][CH2:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)(=[NH:18])=[O:17])[CH3:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Trimethyloxonium fluoroborate (3.81 g, 25.6 mmol) was added to a solution of N,N-diethyl-3-[S-(4-nitrophenyl)sulfonimidoyl]-1-propanamine (7.7 g, 25.6 mmol) in methylene chloride (50 mL) maintained at -20° C. After 15 min the reaction mixture was warmed to 0° C. for 30 min and then to ambient temperature for 1 h. Water (100 mL) was added to the reaction mixture, and the reaction mixture was made basic with 10% sodium hydroxide. The biphasic mixture containing insoluble material was filtered. The solid that was collected by filtration was recrystallized from a methanol/ethanol mixture. The white solid that formed was collected by filtration to give 0.51 g(4.9%), mp 125°-126.5° C.
Workup
- temperatureAfter 15 min the reaction mixture was warmed to 0° C. for 30 min
- additionThe biphasic mixture containing insoluble material
- filtrationwas filtered
- filtrationThe solid that was collected by filtration
- customwas recrystallized from a methanol/ethanol mixture
- customThe white solid that formed
- filtrationwas collected by filtration
- customto give 0.51 g(4.9%), mp 125°-126.5° C.
Sources & evidence
- ORD record
- ord-12d99970b54f472280e3b1dd89f61508
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05187189
Reaction notes
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