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K. C. Majumdar, S. K. Samanta
PAPER
1H NMR (CDCl3, 300 MHz): = 2.91 (s, 3 H, NCH3), 4.01 (t,
J = 1.6 Hz, 2 H, NCH2), 4.8 (t, J = 1.6 Hz, 2 H, OCH2), 6.20 (s, 1 H,
H-3), 6.9–7.4 (m, 6 H, ArH), 7.8 (d, J = 8 Hz, 1 H, H-5).
1H NMR (CDCl3, 300 MHz): = 2.8 (t, J = 6 Hz, 2 H, NCH2CH2),
3.0 (s, 3 H, NCH3), 3.3 (t, J = 6 Hz, 2 H, NCH2), 6.7–7.4 (m, 7 H,
ArH), 7.7 (d, J = 8 Hz, 1 H, H-10), 8.1 (s, 1 H, =CHOAr).
MS m/z: 404, 408, 406 (M+).
MS m/z: 369, 371 (M+).
Anal. Calcd for C20H15Cl2NO2S: C,59.4, H, 3.71, N, 3.46. Found C,
59.12; H, 3.52; N, 3.21.
Anal. Calcd for C20H16ClNO2S: C, 65; H, 4.3; N, 3.79. Found C,
64.82; H, 4.19; N, 3.51.
Compounds 5a–f and 6a,b; General Procedure
5e
Compounds 4a–f (0.2 g, 0.59 mmol) were refluxed in 1,2-dichlo-
robenzene (2 mL) for 2 h. The mixture was then cooled and directly
subjected to column chromatography over silica gel. 1,2-Dichlo-
robenzene was eluted out with petroleum ether. All the products 5a–
f were obtained when the column was eluted with petroleum ether–
benzene (3:1). Compounds 6a,b followed compounds 5a,b in the
same eluent and were carefully separated. Unchanged starting ma-
terials 4a–f were also carefully eluted out with benzene. The yields
were calculated on the basis of actual conversion of starting materi-
als.
Yield: 81%; viscous liquid; Rf 0.4 (benzene–petroleum ether, 1:3).
UV(EtOH): max (log ) 227 (4.4), 264 (4.0), 352 nm (3.6).
IR (film): 1230, 1480, 1590, 1710, 2970 cm–1.
1H NMR (CDCl3, 300 MHz): = 2.9 (t, J = 6 Hz, 2 H, NCH2CH2),
3.1 (s, 3 H, NCH3), 3.4 (t, J = 6 Hz, 2 H, NCH2), 7.2–7.5 (m, 7 H,
ArH), 7.7 (d, J = 8 Hz, 1 H, H-10), 8.2 (s, 1 H, =CHOAr).
MS m/z: 369, 371 (M+).
Anal. Calcd for C20H16ClNSO2: C, 65.00; H, 4.30; N, 3.79. Found
C, 64.89; H, 4.18; N, 3.48.
5a
5f
Yield: 65%; viscous liquid; Rf 0.4 (benzene–petroleum ether,1:3).
Yield: 75%; viscous liquid; Rf 0.4 (benzene–petroleum ether, 1:3).
UV (EtOH): max (log ) 223 (4.4), 269 (4.2), 397 nm (4).
IR (film): 1240, 1460, 1570, 1710, 2960 cm–1.
1H NMR (CDCl3, 300 MHz): = 2.8 (t, J = 6 Hz, 2 H, NCH2CH2),
3.0 (s, 3 H, NCH3), 3.37 (t, J = 6 Hz, 2 H, NCH2), 7.0–7.5 (m, 8 H,
ArH), 7.7 (d, J = 8 Hz, 1 H, H-10), 8.2 (s, 1 H, =CHOAr).
UV (EtOH): max (log ) = 232 (4.4), 292 (3.9), 347 nm (3.5).
IR (film): 1250, 1470, 1580, 1710, 2950 cm–1.
1H NMR (CDCl3, 300 MHz): = 2.9 (t, J = 6 Hz, 2 H, NCH2CH2),
3.1 (s, 3 H, NCH3), 3.4 (t, J = 6 Hz, 2 H, NCH2), 7.1–7.3 (m, 7 H,
ArH), 7.7 (d, J = 8 Hz, 1 H, H-10), 8.1 (s, 1 H, =CHOAr).
MS m/z: 335 (M+);
MS m/z: 404, 408, 406 (M+).
Anal. Calcd for C20H17NO2S: C, 71.64; H, 5.07; N, 4.17. Found C,
71.39; H, 4.81; N, 3.87.
Anal. Calcd for C20H15Cl2NO2S: C, 59.4, H, 3.71, N, 3.46. Found C,
59.29; H, 3.62; N, 3.25.
5b
6a
Yield 62%; viscous liquid; Rf 0.4 (benzene–petroleum ether, 1:3).
Yield: 25%; viscous liquid; Rf 0.3 (benzene–petroleum ether, 1:3).
UV(EtOH): max (log ) 224 (4.4), 269 (4.1), 379 nm (3.8).
IR (Film): 1230, 1500, 1600, 1710, 2960 cm–1.
1H NMR (CDCl3, 300 MHz): = 2.25 (s, 3 H, ArCH3), 2.8 (t, J = 6
Hz, 2 H, NCH2CH2), 3.0 (s, 3 H, NCH3), 3.3 (t, J = 6 Hz, 2 H,
NCH2), 6.9–7.3 (m, 7 H, ArH), 7.8 (d, J = 8 Hz, 1 H, H-10), 8.2 (s,
1 H, =CHOAr).
UV (EtOH): max (log ) = 220 (4.4), 347 nm (3.6).
IR (film): 1230, 1480, 1600, 2960 cm–1.
1H NMR (CDCl3, 300 MHz): = 2.9 (s, 3 H, NCH3), 3.7 (d, J = 4.6
Hz, 2 H, NCH2), 5.1 (d, J = 1.4 Hz, 2 H, OCH2), 5.8 (t, J = 4.6 Hz,
1 H, NCH2CH), 6.9–7.3 (m, 8 H, ArH), 7.9 (d, J = 8 Hz, 1 H, H-10).
MS m/z: 335 (M+).
MS m/z: 349 (M+).
Anal. Calcd for C20H17SNO2: C, 71.64; H, 5.07; N, 4.17. Found C,
71.45; H, 4.91; N, 3.90.
Anal. Calcd for C21H19O2NS: C, 72.20; H, 5.44; N, 4.0. Found C,
71.82; H, 5.31; N, 3.89.
6b
5c
Yield: 20%; viscous liquid; Rf 0.3 (benzene–petroleum ether, 1:3).
Yield: 85%; viscous liquid; Rf 0.4 (benzene–petroleum ether, 1:3).
UV (EtOH): max (log ) = 224 (4.21), 359 nm (3.6).
IR (film): 1240, 1490, 1600, 2960 cm–1.
UV (EtOH): max (log ) 221 (4.3), 359 nm (3.66).
IR (film): 1240, 1490, 1590, 1710, 2970 cm–1.
1H NMR (CDCl3, 300 MHz): = 2.26 (s, 3 H, ArCH3), 2.9 (s, 3 H,
NCH3), 3.7 (d, J = 4.6 Hz, 2 H, NCH2), 5.0 (d, J = 1.4 Hz, 2 H,
OCH2), 5.8 (t, J = 4.6 Hz, 1 H, NCH2CH), 6.8–7.4 (m, 7 H, ArH),
7.9 (d, J = 8 Hz, 1 H, H-10).
1H NMR (CDCl3, 300 MHz): = 2.27 (s, 3 H, ArCH3), 2.8 (t, J = 6
Hz, 2 H, NCH2CH2), 3.0 (s, 3 H, NCH3), 3.3 (t, J = 6 Hz, 2 H,
NCH2), 6.91–7.3 (m, 7 H, ArH), 7.8 (d, J = 8 Hz, 1 H, H-10), 8.2 (s,
1 H, =CHOAr).
MS m/z: 349 (M+).
MS m/z: 349 (M+).
Anal. Calcd for C21H19NO2S: C, 72.20; H, 5.44; N, 4.00. Found C,
72.05; H, 5.21; N, 3.84.
Anal. Calcd for C21H19NO2S: C, 72.20; H, 5.44; N, 4.0. Found C,
71.88; H, 5.31; N, 3.72.
5d
Acknowledgement
Yield: 82%; viscous liquid; Rf 0.4 (benzene–petroleum ether, 1:3).
UV (EtOH): max (log ) 232 (4.4), 292 (3.9), 374 nm (3.5).
IR (film): 1240, 1470, 1710, 2960 cm–1.
We are thankful to the CSIR (New Delhi) for financial assistance.
One of us (S.K.S.) is grateful to the CSIR (New Delhi) for a fel-
lowship.
Synthesis 2002, No. 1, 121–125 ISSN 0039-7881 © Thieme Stuttgart · New York