Dimethylamine → 4-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N,N'-trimethyl-benzene-sulfonimidamide
Reaction equation
[CH3:1][NH:2][S:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:7][CH:6]=1)=[O:4].ClO[C:25](C)(C)C.[CH3:29][NH:30]C.O>C(#N)C>[O:22]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[N:12]1[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([S:3](=[N:30][CH3:29])([N:2]([CH3:25])[CH3:1])=[O:4])=[CH:10][CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzenesulfinic acid methylamide (preparation 60b, 250 mg, 0.795 mmol) in acetonitrile is cooled at 0° C. in an ice bath and treated with tert-butyl hypochlorite (100 μL, 0.88 mmol). After 15 min dimethylamine (2 M in tetrahydrofuran, 600 μL, 1.2 mmol) is added and the mixture is warmed to room temperature. Water is added, and the mixture is extracted twice with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 7:3 to ethyl acetate). Yield: 284 mg (99% of theory). ESI mass spectrum: [M+H]+=358; r.t. HPLC: 0.43 min (X012_S01).
Workup
- temperaturethe mixture is warmed to room temperature
- extractionthe mixture is extracted twice with dichloromethane
- dry with materialThe combined organic layers are dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 7:3 to ethyl acetate)
- customr.t
- custom0.43 min (X012_S01)
Sources & evidence
- ORD record
- ord-f5e32827a84b4964a93a10e82a927088
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346794B1
Reaction notes
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