J.-P. Vors et al. / Tetrahedron 59 (2003) 555–560
Table 5. Comparison of the experimental and calculated dhkl distances and intensities
559
dhkl Exp
Intensity
dhkl Exp
Intensity
h
k
l
dhkl Calcd.
Closest dhkl exp
9.8214
8.0021
7.6442
7.3093
13.2
38.3
75.6
109.2
3.3583
3.2154
3.0833
3.0071
148.7
111.6
48.3
33.2
Visible faces in the morphology calculated from the theory of attachment
energies
6.5181
6.2272
6.0410
5.7071
5.3292
5.0574
4.8803
4.7011
4.5088
4.4483
4.3033
4.1948
16.5
25.8
19.1
43.7
19.2
38.3
93.5
16.1
128.5
127.7
39.7
26.1
2.8722
2.7878
2.6437
2.5069
2.4524
2.4306
2.3780
2.3521
2.2932
2.2407
2.2090
2.0512
20.9
15.8
40.0
19.9
34.9
31.6
45.8
35.0
19.8
18.2
23.0
5.9
0
1
1
1
0
0
1
1
0
0
0
0
0
21
1
21
2
22
2
22
0
1
1
0
1
1
1
1
1
1
8.0482
8.0382
5.7811
5.7081
5.7057
5.7057
3.3143
3.3143
3.6142
3.6142
8.0021
8.0021
5.7071
5.7071
5.7071
5.7071
3.3583
3.3583
3.6567
3.6567
Other faces
4.0371
3.9050
3.8237
3.6567
3.4288
87.5
30.0
128.3
132.5
144.1
2.0045
1.9110
1.8687
1.7496
1.7145
12.1
15.8
14.3
15.2
18.2
0
1
1
1
1
1
1
0
1
1
0
8.0900
5.7021
5.5982
4.7036
4.6035
8.0021
5.7071
5.7071
4.7011
4.7011
0
21
1
21
˚
˚
˚
System: monoclinic; space group: P21; Z: 2; Cell parameters: a (A)¼8.04, a (8)¼90, b (A)¼8.09, b (8)¼76.99, c (A)¼8.05, g (8)¼90; density dm
(g cm23)¼1.61; lattice energy (kJ mol21)¼2126.
4. Chazalet, M.; Gouot, J. -M.; Peignier, R. PCT Int. Appl. WO
9843480 A1, October 8, 1998; Chem. Abstr. 1998, 129,
299238).
concentrated to dryness and the residue was triturated in
hexane to give 7.1 g (mp 1568C) of 3-(3,5-dichlorophenyl)-
1H-pyrazole. This pyrazole (2.3 g, 0.0152 mol) was chlori-
nated at room temperature in 300 mL of dichloromethane
with 2.07 g (0.016 mol) of N-chlorosuccinimide during 4
days. The reaction mixture was then concentrated and the
residue chromatographed on silica gel (heptane/ethyl
acetate 70/30 v/v) to give 1.4 g of 1 (mp 1928C). Exact
mass, calculated 247.95183, determined by mass spec-
5. Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. The
Tautomerism of Heterocycles; Academic: New York, 1976.
6. Elguero, J.; Katritzky, A. R.; Denisko, O. V. Adv. Heterocycl.
Chem. 2000, 76, 1.
7. Minkin, V. I.; Garnovskii, A. D.; Elguero, J.; Katritzky, A. R.;
Denisko, O. V. Adv. Heterocycl. Chem. 2000, 76, 157.
8. Foces-Foces, C.; Alkorta, I.; Elguero, J. Acta Crystallogr.
Sect. B 2000, 56, 1018.
´
9. Cativiela, C.; Garcıa, J. I.; Elguero, J.; Elguero, E. Gazz. Chim.
Ital. 1991, 121, 477.
1
trometry 247.95437. H NMR (DMSO-d6) 13.58, bs, NH;
8.07, s, C5-H; 7.81, d, J¼1.8 Hz, 2H; 7.61, t, J¼1.8 Hz, 1H.
10. Aguilar-Parrilla, F.; Cativiela, C.; Diaz de Villegas, M. D.;
Elguero, J.; Foces-Foces, C.; Garcia, J. I.; Cano, F. H.;
Limbach, H.-H.; Smith, J. A. S.; Toiron, C. J. Chem. Soc.,
Perkin Trans. 2 1992, 1737.
Acknowledgements
The authors thank Richard Cantegril, Denis Croisat,
Franc¸ois Guigues, Jacques Mortier, from the synthesis
team, and the members of the Scale-up laboratory and of the
Analytical Department from the Aventis CropScience
Research Center in Lyon, who have contributed a lot to
the birth and life of the RPA 406194 project. They also
acknowledge Joel Jaud’s help (CEMES, Toulouse) for
recording the X-ray powder diagram of RPA 406194.
´
11. Abboud, J. L. M.; Cabildo, P.; Can˜ada, T.; Catalan, J.;
Claramunt, R. M.; De Paz, J. L. G.; Elguero, J.; Homan, H.;
Notario, R.; Toiron, C.; Yranzo, G. I. J. Org. Chem. 1992, 57,
3938.
´
12. Lopez, C.; Claramunt, R. M.; Trofimenko, S.; Elguero, J. Can.
J. Chem. 1993, 71, 678.
´
13. Cativiela, C.; Garcıa, J. I.; Fayet, J.-P.; Elguero, J. Bull. Soc.
Chim. Belg. 1995, 104, 383.
´ ´
14. Pierrot, M.; Kenz, A.; Garcıa, M. A.; Lopez, C.; Claramunt,
R. M.; Elguero, J. In preparation.
15. Stothers, J. B. Carbon-13 NMR Spectroscopy; Academic: New
York, 1972; p 197.
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