Chlorosulfonyl isocyanate → Benzyl 4-(carbamoyloxy)-2-methylbenzoate

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Reaktionsgleichung

[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1.ClS([N:23]=[C:24]=[O:25])(=O)=O>ClCCl>[NH2:23][C:24]([O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1)=[O:25]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of phenylmethyl 4-hydroxy-2-methylbenzoate (687 mg, 2.82 mmol) in dichloromethane (8 ml) at 0° C., was added chlorosulfonyl isocyanate (1.20 g, 8.50 mmol). The reaction was allowed to warm to 25° C. and stirred for 20 h. The reaction mixture was concentrated then taken into ethyl acetate and washed with water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexanes/ethyl acetate) to afford phenylmethyl 4-[(aminocarbonyl)oxy]-2-methylbenzoate (356 mg, 89%). 1H NMR (400 MHz, DMSO): 7.91-7.87 (d, 1H), 7.49-7.29 (m, 5H), 7.11-7.00 (m, 4H), 5.31 (s, 2H), 2.52 (s, 3H). MS (EI) for C16H15NO4: 286 (MH+).

Aufarbeitung

concentrationThe reaction mixture was concentrated
washwashed with water
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-d334400bb4f94650bcbf2ca51b49736a
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08012956B2

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