Sodium Carbonate → 2-{4-[4-(Methylsulfonyl)-2-nitroanilino]phenyl}ethanol

HRID 858433Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][OH:24])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][OH:24])=[CH:18][CH:17]=2)=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-5-methylsulfonylnitrobenzene (Kavalek, J.; et al. Collect. Czech. Chem. Commun, 1971, 36, 209., 2 g, 8.5 mmol), 4-aminophenylethyl alcohol (1.4 g, 10.2 mmol) and Na2CO3 (1.4 g, 12.7 mmol) in ethanol was stirred at 100° C. for 16 h. The insoluble matter was removed by filtration and washed with ethanol (100 mL). The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:4) to afford 960 mg (34%) of the title compound as yellow solids: 1H-NMR (CDCl3) δ 9.84 (1H, br.s), 8.82 (1H, d, J=2.1 Hz), 7.79 (1H, dd, J=2.1 Hz, 9.1 Hz), 7.36 (2H, d, J=8.4 Hz), 7.22–7.38 (3H, m), 3.94 (2H, br.s), 3.07 (3H, s), 2.93 (2H, t, J=6.6 Hz).

Workup

customThe insoluble matter was removed by filtration
washwashed with ethanol (100 mL)
concentrationThe filtrate was concentrated
customthe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:4)

Sources & evidence

ORD record: ord-2a7f1b8cd8b54cd8810f86cfbf9f981d
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148234B2

Reaction notes

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