Benzenesulfonyl chloride → 4-(1,1-Dimethylethyl)-benzoic acid, 2-(phenylsulfonyl)hydrazide

HRID 393829

Reaktionsgleichung

[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([NH:11][NH2:12])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CN(C1C=CN=CC=1)C>[C:24]1([S:30]([NH:12][NH:11][C:9](=[O:10])[C:8]2[CH:13]=[CH:14][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

4-tert-Butyl-benzoic acid hydrazide (0.5 g, 2.60 mmol) was dissolved in THF (29 mL). N,N-diisopropylethylamine (1.81 mL, 10.4 mmol) was added, and the reaction was cooled to 0° C. Phenylsulfonyl chloride (0.36 mL, 2.86 mmol) was added followed by DMAP (5 mg, 0.04 mmol). The reaction was allowed to warm to room temperature, and the reactants all dissolved. The solution went from a yellow color to a deep red over the course of 4 hours. The reaction was then concentrated down and purified by flash chromatography eluting with 3:1 hexanes/EtOAc. The desired product was isolated (0.32 g, 37.1%). MS: 333.1 (M+1 for C17H20N2O3S); mp 197-199° C.; TLC: SiO2 Rf=0.56 (1:1 hexane/EtOAc). Analysis C17H20N2O3S: (calc) C, 61.42; H, 6.06; N, 8.43. (found) C, 61.38; H, 6.09; N, 8.27. IR (KBr, cm−1) 3213, 2965, 1648, 1403, 1349, 1179. 1H NMR (400 MHz, CDCl3) δ 1.29 (s, 9H), 7.39-7.55 (m, 8H), 7.92-7.93 (m, 2H), 8.06 (s, 1H).

Aufarbeitung

temperatureto warm to room temperature
customwent from a yellow color to a deep red over the course of 4 hours
concentrationThe reaction was then concentrated down
custompurified by flash chromatography
washeluting with 3:1 hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-f622c312826c4955b8b81db1e9b3f7e5
Quelldatensatz: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06809119B2

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