Chlorotrimethylsilane → 1H-Isoindole-1,3(2H)-dione, 2-(trimethylsilyl)-
Reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C(N(CC)CC)C.[CH3:19][Si:20]([CH3:23])([CH3:22])Cl>C(#N)C>[CH3:19][Si:20]([CH3:23])([CH3:22])[N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
250 g (1.7 moles) of phthalimide were suspended in 2.75 liter of acetonitrile and after 250 ml (1.8 moles) of triethylamine were added, the mixture was heated to gentle reflux. 250 ml (1.97 moles) of trimethylchlorosilane were added in 10 minutes and the reaction mixture was then concentrated to a thick paste. 2.5 liter of light petroleum (80°-110° C) were added, the triethylammonium hydrochloride was filtered off and washed with 500 ml of light petroleum. The filtrate ans washings were combined and concentrated until crystallization started. After cooling in the refrigerator for several hours, N-trimethylsilylphthalimide was isolated by filtraton, washed with a small portion of light petroleum (40°-60° C) and dried in vacuo. The compound was further purified by recrystallization from ligroin (80°-100° C). PMR: 0.51 (s, 9); 7.73 (centre of super imposed signals, 4).
Workup
- temperaturethe mixture was heated to gentle reflux
- concentrationthe reaction mixture was then concentrated to a thick paste
- addition2.5 liter of light petroleum (80°-110° C) were added
- filtrationthe triethylammonium hydrochloride was filtered off
- washwashed with 500 ml of light petroleum
- concentrationconcentrated until crystallization
- temperatureAfter cooling in the refrigerator for several hours
Sources & evidence
- ORD record
- ord-d522390bf40a4e1f986b0028b6232c9b
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04046761
Reaction notes
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