Ethanol → (4-(N-cyano-S-methylsulfonimidoyl)phenyl)methanamine

HRID 527343Notes

Reaction equation

[C:1]([N:3]=[S:4]([C:7]1[CH:24]=[CH:23][C:10]([CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:9][CH:8]=1)([CH3:6])=[O:5])#[N:2].NCCN.O1CCCC1.C(O)C>C(#N)C>[C:1]([N:3]=[S:4]([C:7]1[CH:24]=[CH:23][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=1)([CH3:6])=[O:5])#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-(4-(N-cyano-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione (preparation 6c, 684 mg, 2.02 mmol) and 1,2-diaminoethane (243 μL, 219 mg, 3.64 mmol) in a mixture of acetonitrile (8 mL), tetrahydrofuran (4 mL) and ethanol (4 mL) is heated at 60° C. for 5 h. All volatiles are removed under reduced pressure and the residue is suspended in dichloromethane. The mixture is filtered and the filtrate is concentrated under reduced pressure. Yield: 326 mg (77% of theory); ESI mass spectrum: [M+H]+=210; r.t. HPLC: 0.223 min (V001_007).

Workup

customAll volatiles are removed under reduced pressure
filtrationThe mixture is filtered
concentrationthe filtrate is concentrated under reduced pressure
customr.t
custom0.223 min (V001_007)

Sources & evidence

ORD record: ord-2704307c8a644716af6d91a5150e41c9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346794B1

Reaction notes

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