SYNTHESIS OF METHYL p-ALKOXYPHENYLCARBAMATES
69
C Carom). 1H NMR spectrum, , ppm: 8.48 br.s
(1H, NH), 7.45 d (2H, Harom, J = 8.6 Hz), 6.90 d
(2H, Harom, J = 8.6 Hz), 6.05 m (1H, 5-H), 5.41 d
(1H, 4-H, J = 17 Hz), 5.22 d (1H, 4-H, J = 11 Hz),
4.55 d (2H, OCH2, J = 4.3 Hz), 3.68 s (3H, OMe).
Found, %: C 64.11; H 6.13; N 6.42. C11H13NO3.
Calculated, %: C 63.77; H 6.28; N 6.76.
3355 (NH); 1710 (C O); 1605, 1539 (C Carom).
Found, %: C 61.96; H 7.84; N 9.21. C16H24N2O4.
Calculated, %: C 62.34; H 7.79; N 9.09.
Compound VI was converted into the correspond-
ing hydrochloride by treatment of a solution of 0.4 g
(1.3 mmol) of free base VI in 7 ml of dry benzene
with a solution of HCl in diethyl ether. Yield 0.43 g
(95%), mp 153 C. Found, %: C 56.03; H 7.11;
N 8.02. C16H25ClN2O4. Calculated, %: C 55.73;
H 7.26; N 8.13.
Methyl p-(4-bromobutoxy)phenylcarbamate
(IIIb) was synthesized in a similar way from 0.84 g
(5.03 mmol) of carbamate I, 0.6 ml (4.97 mmol) of
freshly distilled 1,4-dibromobutane (IIb), 0.69 g
(5 mmol) of potassium carbonate, and 3 ml of acetone.
Yellow crystals, yield 1.2 g (81%), mp 105 C (from
REFERENCES
1
1. Maksimova, T.N., Shtonda, N.P., Velikorodov, A.V.,
and Khabarova, O.V., Izv. Vyssh. Uchebn. Zaved.,
Ser. Khim. Khim. Tekhnol., 1987, vol. 30, no. 2,
pp. 132 133.
2. Gregani, F., Durindai, J., and Chalikov, S.Ch., Farm.
Obz., 1990, vol. 59, no. 7, pp. 297 300.
diethyl ether). IR spectrum, , cm : 3355 (NH); 1710
(C O), 1620, 1555, 1530 (C Carom); 665 (C Br).
Found, %: C 47.56; H 5.03; N 5.01. C12H16BrNO3.
Calculated, %: C 47.68; H 5.30; N 4.64.
3-Aryl-5-(p-methoxycarbonylaminophenoxy-
methyl)-4,5-dihydroisoxazoles Va Vd. A mixture of
1.35 mmol of carbamate IIIa, 1.35 mmol of benzalde-
hyde oxime IVa IVd, and 1.35 mmol of N-chloro-
benzenesulfonamide sodium salt trihydrate in 25 ml
of anhydrous ethanol was refluxed for 6 h. The prod-
ucts were isolated by the procedure reported in [6] and
were purified by recrystallization from chloroform.
3. Czech. Patent no. 276205, 1992; Ref. Zh., Khim.,
1994, no. 4O15P.
4. Yukinori, N., Yoshimoto, A., Takaniso, M., Nobu-
masa, I., Yoshikazu, F.M., Hiroyuki, I., and Massa-
kazu, M., Nippon Kagaku Kaishi, 1993, no. 6,
pp. 719 727.
5. Weygand Hilgetag
organisch-chemische
Experi-
Methyl p-(4-morpholinobutoxy)phenylcarba-
mate (VI). Freshly distilled morpholine, 0.26 ml
(3 mmol), was added to a solution of 0.3 g (1 mmol)
of carbamate IIIb in 12 ml of dry benzene, and the
mixture was kept for 24 h at room temperature. The
precipitate of morpholine hydrochloride was filtered
off, and the solvent and excess amine were removed
under reduced pressure. The residue was recrystallized
from benzene hexane (1:1). Yield 0.2 g (64%), color-
mentierkunst, Hilgetag, G. and Martini, A., Eds.,
Leipzig: Johann Ambrosius Barth, 1964, 3rd ed.
6. Velikorodov, A.V. and Mochalin, V.B., Russ. J. Org.
Chem., 2001, vol. 37, no. 1, pp. 83 86.
7. Barnet, K., Angew. Chem., 1985, vol. 97, no. 3,
pp. 231 232.
8. Grinev, A.N., Panishcheva, E.K., Cherkasova, A.A.,
Stolyarchuk, A.A., Ivanova, N.I., Lysaya, T.I., and
Storozhuk, B.G., Khim.-Farm. Zh., 1983, vol. 17,
no. 8, pp. 940 946.
1
less crystals, mp 91 92 C. IR spectrum, , cm :
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 1 2002