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

HRID 724074Notes

Reaction equation

HRID 724074 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

5

Reactant 3

HCID 10340Sodium CarbonateHCID 667964-Chloro-3-nitrophenyl methyl sulfoneHCID 669044-Aminophenethyl alcohol

Product 1

HCID 218764282-{4-[4-(Methylsulfonyl)-2-nitroanilino]phenyl}ethanolYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

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

Sources & evidence

ORD record
ord-91a1cce970064bb99d59837f5ffa2fb4
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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