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Dimethylamine → 4-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N,N'-trimethyl-benzene-sulfonimidamide

HRID 527363
Notes
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Reaction equation

HRID 527363 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 521297Tert-Butyl hypochloriteHCID 867116344-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzenesulfinic acid methylamide

Product 1

HCID 899787664-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N,N'-trimethyl-benzene-sulfonimidamide

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

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

  1. temperaturethe mixture is warmed to room temperature
  2. extractionthe mixture is extracted twice with dichloromethane
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 7:3 to ethyl acetate)
  6. customr.t
  7. custom0.43 min (X012_S01)

Sources & evidence

ORD record
ord-f5e32827a84b4964a93a10e82a927088
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346794B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes