Sulfuryl chloride → tert-butyl N-[3-(chlorosulfonyl)phenyl]-N-methylcarbamate

HRID 29190

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:6].C([Li])CCC.[S:22](Cl)([Cl:25])(=[O:24])=[O:23]>C1COCC1>[C:10]([O:9][C:7]([N:5]([CH3:6])[C:4]1[CH:14]=[CH:15][CH:16]=[C:2]([S:22]([Cl:25])(=[O:24])=[O:23])[CH:3]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

3-Bromo-N-tert-butoxycarbonyl-N-methylaniline (0.358 g, 1.2 mmol) was dissolved in freshly distilled THF (5 ml) under a N2 atmosphere. The solution was chilled to −78° C. and n-butyl lithium (0.750 ml, 2.0 M solution in cyclohexane, 1.5 mmol) was added. After 15 minutes, sulfuryl chloride (0.121 ml, 1.5 mmol) was added and the reaction was allowed to warm to room temperature and stirring was continued overnight. THF was removed by evaporation and the resulting residue was diluted in EtOAc. Organic phase was washed with H2O and brine before being dried with MgSO4. The solvent was removed in vacuo. Purification by flash chromatography (1:19/EtOAc/Hex gradient to 1:9 and then to 1:4). Recovered 0.089 g (23%) of the product as a colorless oil. Rf=0.14 (1:9 EtOAc/Hex). 1H NMR (CDCl3) 7.96 (1H,s), 7.80 (1H,d), 7.68 (1H,d), 7.57 (1H,t), 3.33 (3H,s), 1.50 (9H,s).

Aufarbeitung

temperatureto warm to room temperature
waitwas continued overnight
customTHF was removed by evaporation
additionthe resulting residue was diluted in EtOAc
washOrganic phase was washed with H2O and brine
dry with materialbefore being dried with MgSO4
customThe solvent was removed in vacuo
customPurification by flash chromatography (1:19/EtOAc/Hex gradient to 1:9
customRecovered 0.089 g (23%) of the product as a colorless oil

Quellen und Nachweise

ORD-Eintrag: ord-950b4dc6d8054b6cb3d25456521aec7b
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07419967B2

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