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2
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1842740213
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Syakhovich V.E., Parul D.A., Ruta E.Y., Bushuk B.A., and Bokut S.B. Biochem. Biophys. Res. Commun. 317 3 (2004) 76
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(2004)
Biochem. Biophys. Res. Commun.
, vol.317
, Issue.3
, pp. 76
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Syakhovich, V.E.1
Parul, D.A.2
Ruta, E.Y.3
Bushuk, B.A.4
Bokut, S.B.5
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9
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0001322053
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Carmichael A.J., Eale M.J., Holberg J.D., Mcormav P.B., and Seddon K.R. Org. Lett. 1 7 (1999) 997
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(1999)
Org. Lett.
, vol.1
, Issue.7
, pp. 997
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Carmichael, A.J.1
Eale, M.J.2
Holberg, J.D.3
Mcormav, P.B.4
Seddon, K.R.5
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13
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67349272694
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Preparation of 5,5′-bis-8-phenylamino-1-naphthylsulfonic (bis-ANS) potassium salt (3) in ionic liquids: to 8-phenylamino-1-naphthalenesulfonic acid (ANS) potassium salt (2, 26 g, 0.074 mol) was dissolved in concentrated hydrochloric acid (100 mL) and cooled in an ice bath. The sodium nitrite (56 mL, 0.2 mol/L) was added to the solution dropwise with vigorous stirring. The mixture was warmed to room temperature and added ionic liquid (0.1 mol, The resulting solution was heated to 65-70 °C and stirred for 4 h. The reaction mixture was cooled to room temperature and extracted with chloroform (100 mL × 3, The combined organic layer was washed with saturated sodium bicarbonate solution and concentrated to give a green powder (a mixture of monomer and dimer potassium salts, The target product, bis-ANS was obtained on a silica gel column, eluent: ethyl acetate to acetone: methanol (5:1, as a purple solid 28 g, 56
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Preparation of 5,5′-bis-8-phenylamino-1-naphthylsulfonic (bis-ANS) potassium salt (3) in ionic liquids: to 8-phenylamino-1-naphthalenesulfonic acid (ANS) potassium salt (2) (26 g, 0.074 mol) was dissolved in concentrated hydrochloric acid (100 mL) and cooled in an ice bath. The sodium nitrite (56 mL, 0.2 mol/L) was added to the solution dropwise with vigorous stirring. The mixture was warmed to room temperature and added ionic liquid (0.1 mol). The resulting solution was heated to 65-70 °C and stirred for 4 h. The reaction mixture was cooled to room temperature and extracted with chloroform (100 mL × 3). The combined organic layer was washed with saturated sodium bicarbonate solution and concentrated to give a green powder (a mixture of monomer and dimer potassium salts). The target product, bis-ANS was obtained on a silica gel column, eluent: ethyl acetate to acetone: methanol (5:1), as a purple solid (28 g, 56%).
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14
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67349216757
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The product 3 obtained in this study was characterized: (m.p. 1H NMR 13C NMR ESIMS EA) m.p. >250 °C. 1H NMR (300 MHz, DMSO-d6 δppm, 8.21 (dd, 2H, J, 5.7, 1.2 Hz, C4-H, 7.58 (d, 2H, J, 5.7 Hz, C2-H, 7.31 (d, 2H, J, 6.6 Hz, C6-H, 7.28 (dd, 2H, J, 6.6, 1.2 Hz, C3-H, 7.14-7.24 (m, 8H, Ar-Ho,m) 6.94-7.09 (d, 2H, J, 5.6 Hz, C7-H, 6.79 (m, 2H, Ar-Hp, 13C NMR (300 MHz, DMSO-d6 δppm, 145.2 (C-11, 144.1 (C-8, 140.0 (C-1, 136.6 (C-10, 131.8 (CH-4, 130.0 (C-5, 129.7 (CH-13, 128.9 (CH-6, 127.1 (CH-2, 124.8 (CH-3, 123.0 (C-9, 119.9 (CH-12, 117.6 (CH-14, 114.8 CH-7, ESIMS m/z 673 [M, Anal. Calcd. for C32H22K2N2O6S2: C 57.12, H 3.30, K 11.62, N 4.16, O 14.27, S 9.53; Found: C 57.02, H 3.36, K 11.43, N 4.01, O 14.31, S 9.26
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2: C 57.12, H 3.30, K 11.62, N 4.16, O 14.27, S 9.53; Found: C 57.02, H 3.36, K 11.43, N 4.01, O 14.31, S 9.26%.
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