Triethylamine → HCID 66920960, compound

HRID 2066335Notes

Reaction equation

Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].Br[CH:9]([OH:11])[CH3:10].[CH3:12][Si:13]([CH:16]([NH2:21])[Si:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:14].C(N(CC)CC)C>ClCCl>[CH3:12][Si:13]([CH:16]([NH:21][S:2]([N:5]1[CH2:10][CH2:9][O:11][C:6]1=[O:7])(=[O:4])=[O:3])[Si:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To 2.18 ml of chlorosulfonyl isocyanate in 10 ml of dichloromethane is added dropwise, at 0° C., a solution of 1.77 ml of bromoethanol in 10 ml of dichloromethane. The reaction medium is stirred for 10 minutes at 0° C. and then added dropwise to a solution of 4.38 grams of bis(trimethylsilyl)methylamine and 3.51 ml of triethylamine in 40 ml of dichloromethane at 0° C. After warming to 20° C. and stirring for 4 hours, the reaction mixture is cooled to 0° C. and 10.5 ml of triethylamine are then added dropwise. The reaction mixture is then stirred overnight at room temperature. It is then diluted with dichloromethane and washed 3 times with dilute hydrochloric acid. The organic phase is then washed once with saturated aqueous NaCl solution and then dried over sodium sulfate and concentrated under reduced pressure to give a white solid, 2-oxooxazolidine-3-sulfonic acid [bis(trimethylsilanyl)methyl]amide (65% yield).

Workup

temperatureAfter warming to 20° C.
stirringstirring for 4 hours
temperaturethe reaction mixture is cooled to 0° C.
stirringThe reaction mixture is then stirred overnight at room temperature
washwashed 3 times with dilute hydrochloric acid
washThe organic phase is then washed once with saturated aqueous NaCl solution
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-88cdd496e0ba4fde8d1557f44031cc6f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293256B2

Reaction notes

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