168
J Chem Crystallogr (2010) 40:165–168
Scheme 2 Synthesis of
3-(4-methoxy-benzylidene)-
isothiochroman-4-one (6)
NaS-CH2-CO2Et
HCl/CH3CO2H
(50/50)
O
O
S
S
H
S
Cl
S
EtOH/H2O (50/50)
O
O
2
3
1
SOCl2
O
O
H
O
H
O
O
AlCl3
S
Cl
O
4
5
6
Transparent crystals. Yield 87%. M.p. = 93–95 °C. IR
(nujol, m cm-1): 1,647 (C=O), 1,570 (C=C). 1H NMR
(300 MHz, CDCl3) d ppm: 8.1 (s, 1H, C10–H), 6.1–8.0 (m,
8H, 2 Ph), 3.9 (s, 2H, SCH2), 3.8 (s, 3H, OCH3).
The 4-phenyl-3-thiabutanoate-ethyle (2), 4-phenyl-3-
thiabutanoic acid (3), chloride 4-phenyl-3-thiabutanoic
acid (4) and isothiochroman-4-one (5) have been prepared
as described in literature.
Data collection: APEX2 [14]. Cell refinement: APEX2.
Data reduction: SAINT. Program(s) used to solve structure:
SIR97 [15]. Program(s) used to refine structure: SHEL-
XL97 [16]. Molecular graphics: ORTEP-3 for Windows
[17]. Software used to prepare material for publication:
WinGX [18].
Acknowledgments This work was supported by the Program du
Projet Global de Recherche de l’Universite0 Mohamed Premier
d’Oujda ‘PGR-BH-20050 and PARS CO4 Grants from the Ministry
of National Education of Morocco.
4-Phenyl-3-Thiabutanoate Ethyle (2)
Yield = 85%. Eb = 114 °C. IR (nujol) m(cm-1): 1,720
(C=O). 1H NMR (CDCl3) d (ppm): 1.23 (t, 3H, CH3–CH2,
J = 7 Hz); 3.02 (s, 2H, 2H2); 3.80 (s, 2H, 2H4); 4.10 (q,
2H, CH3–CH2, J = 7 Hz); 7.25 (m, 5H, ph).
References
1. Bennani B, Kerbal A, Larbi NB, Hadda TB (2004) Synthesis and
application of spiro-isoxazolines as new anti-tubercular agents.
Moroccan Patent, Casablanca, N 2769
4-Phenyl-3-Thiabutanoic Acid (3)
2. Bennani B, Kerbal A, Larbi NB, Hadda TB (2004) Synthesis and
application of isothiochromeno[3,4-e][1,2]oxazines (TCO) as
new anti-tumoral agents. Moroccan Patent, Casablanca, N 2771
3. Bennani B, Kerbal A, Larbi NB, Hadda TB (2004) Synthesis and
application of some spiro-isoxazolines as new anti-HIV agents.
Moroccan Patent, Casablanca, N 2770
Yield = 42%; mp = 64 °C. IR (KBr): m(cm-1): 2,300–
3,300 (OH); 1,695 (C=O). 1H NMR (CDCl3) d (ppm): 3.15
(s, 2H, H2); 3.85 (s, 2H, 2H4); 10.20 (s, 1H, OH); 7.35 (m,
5H, Ph).
4. Bennani B, Kerbal A, Daoudi M, Baba BF, Houari GA, Jalbout
AF, Mimouni M, Benazza M, Demailly G, Akkurt M, Yıldırım
¨
SO, Hadda TB (2007) ARKIVOC xvi:19–40
Chloride 4-Phenyl-3-Thiabutanoic Acid (4)
5. Lesser R, Mehrlander A (1923) Ber 56:1642–1648
6. Brown JV, Weissbach K (1929) Chem Ber 62:2416–2425
7. Gagnant P, Gagnant D (1959) Bull Soc Chim Fr, 1998
8. Houari GA, Kerbal A, El Bali B, Bolte M (2005) Acta Cryst
E61:o3330–o3333
9. Thibault J (1971) Ann Chim (Paris) 6:381
10. Pulman DA, Whiting DA (1973) J Chem Soc Perkin Trans 1
1(4):410–418
Yield = 80%. Eb = 125 °C. IR (nujol) m(cm-1): 1,790
1
(C=O). H NMR (CDCl3) d(ppm): 3.45 (s, 2H, 2H2); 3.75
(s, 2H, 2H4); 7.25 (m, 5H, Ph).
Isothiochroman-4-One (5)
11. Allen FH (2002) Acta Cryst B58:380–388
12. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354–1358
13. Nardelli M (1983) Comput Chem 7:95–98
14. Bruker (2005) APEX2 (Version 2.1) and SAINT (Version
7.23A). Bruker AXS Inc., Madison
15. Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo
C, Guagliardi A, Moliterni AGG, Polidori G, Spagna R (1999)
J Appl Cryst 32:115–119
White crystals. Yield = 50% . Eb = 138 °C. F = 60 °C.
1
IR (KBr): m(cm-1): 1,670 (C=O). H NMR (CDCl3): 3.55
(s, 2H, 2H3); 3.95 (s, 2H, 2 H1); 7.15–7.55 (m, 3H, Ph);
8.10 (m, 1H).
H atoms were geometrically located in calculated posi-
tions and treated as riding on their parent atoms, with
˚
C–H = 0.93–0.97 A, and with Uiso(H) = 1.2Ueq(C) and
16. Sheldrick GM (2008) Acta Cryst 64:112–122
17. Farrugia LJ (1997) J Appl Cryst 30:565
18. Farrugia LJ (1999) J Appl Cryst 32:837–838
U
iso(H) = 1.5Ueq(C) for methyl group.
123