Formaldehyde → 2-(4-(N,S-Dimethylsulfonimidoyl)benzyl)isoindoline-1,3-dione

HRID 527376Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:7][CH:6]=1)(=[NH:4])=[O:3].[CH2:23]=O>C(O)(=O)C>[CH3:23][N:4]=[S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:21][CH:22]=1)([CH3:1])=[O:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(4-(S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione (preparation 17b, 200 mg, 63.6 mmol) and paraformaldehyde (115 mg, 1.27 mmol) in acetic acid (2 mL) is heated in a microwave at 100° C. for 4 h. The mixture is concentrated under reduced pressure, and the residue is purified by flash chromatography on silica (gradient dichloromethane to dichloromethane/methanol 95:5). Yield: 189 mg (90% of theory); ESI mass spectrum: [M+H]+=329; r.t. HPLC: 0.45 min (X011_S03).

Workup

concentrationThe mixture is concentrated under reduced pressure
customthe residue is purified by flash chromatography on silica (gradient dichloromethane to dichloromethane/methanol 95:5)
customr.t
custom0.45 min (X011_S03)

Sources & evidence

ORD record: ord-abbeccca1f1c438cbd71593006f7d70e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346794B1

Reaction notes

Loading…