(Diethylamino)trimethylsilane → (S)-trimethyl{[methyl(oxo)phenyl-lambda6-sulfanylidene]amino}silane

HRID 391566

Reaction equation

[CH3:1][S@:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[NH:4])=[O:3].[CH3:11][Si:12](N(CC)CC)([CH3:14])[CH3:13]>C(#N)C>[CH3:11][Si:12]([CH3:14])([CH3:13])[N:4]=[S@@:2]([CH3:1])(=[O:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred pre-warmed solution of (S)-(+)-S-methyl-S-phenylsulphoximine (3 g, 18.7 mmol) in acetonitrile (2 mL) at 65° C. was added (trimethylsilyl)diethylamine (4.12 g, 21.1 mmol) dropwise via a syringe. The reaction was maintained at 65° C. and stirred for 3 hours. Additional amount of (trimethylsilyl)diethylamine (2 mL, 10.2 mmol) was added and the reaction mixture was stirred at 65° C. overnight. The reaction was then concentrated under reduced pressure and dried under vacuum to give the title compound. This material was used directly in next step of the synthesis without further purification.

Workup

stirringthe reaction mixture was stirred at 65° C. overnight
concentrationThe reaction was then concentrated under reduced pressure
customdried under vacuum

Sources & evidence

ORD record: ord-8440d5b05f374f379ffa4ec1ef4a9cee
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383825B2

Linked notes

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