1162
X. Xu et al. / Journal of Fluorine Chemistry 125 (2004) 1159–1162
3.3.5. 2-(4-Fluorophenylimino)-4-ethyl-4-hydroxymethyl-
thiazolidine (3e)
231 (36.64) [M–C3H7O], 172 (6.08), 102 (24.29), 87 (9.46).
HRMS calculated for C12H13F3N2OS: 290.0701; found:
290.0702.
2-(4-Fluorophenylimino)-4-ethyl-4-hydroxymethyl-thia-
zolidine (3e) yield 42%, mp 154–155 8C. 1H NMR
(CD3COCD3, 500 MHz) d: 0.99 (t, 3H, J ¼ 7.5 Hz, CH3),
1.69 (m, 2H, CH2), 3.06 (d, 1H, J ¼ 10.9 Hz, Ha(b)-5), 3.36
(d, 1H, J ¼ 10.9 Hz, Hb(a)-5), 3.52 (d, 1H, J ¼ 10.8 Hz,
3.3.9. 2-(2,3,4-Trifluorophenylimino)-4,4-dimethyl-
thiazolidine (3i)
2-(2,3,4-Trifluorophenylimino)-4,4-dimethyl-thiazolidine
1
H
a(b)–CH2OH), 3.59 (d, 1H, J ¼ 10.8 Hz, Hb(a)–CH2OH),
(3i) yield 73%, mp 195–196 8C. H NMR (CD3COCD3,
0
0
0
0
0
0
0 0
7.00 (t, 2H, J2 3 ¼ J6 5 ¼ 8:9 Hz, J4 5 ¼ J4 3 ¼ 8:8 Hz, H-
30 and H-50), 7.49 (br s, 1.7H, H-20 and H-60). IR (KBr)
(cmꢀ1): 3300 (OH), 3100 (NH), 2875, 1640 (C¼N), 1500
(Ph), 1200, 1050, 850. MS (EI, 70 eV) m/z (%): 254 (5.61)
[M], 223 (100.00) [M–CH2OH], 195 (4.31) [M–HCHO–
C2H5], 102 (23.28). HRMS calculated for C12H15FN2OS:
254.0889; found: 254.0880.
500 MHz) d: 1.43 (s, 6H, CH3), 3.22 (s, 2H, H-5), 6.81
(br s, 0.36H, H-20 and H-60), 7.10 (q, 1H, J4 5 ¼ 8:9 Hz,
0
0
J6 5 ¼ 8:9 Hz, J3 5 ¼ 8:3 Hz, H-50). IR(KBr) (cmꢀ1): 3150
(NH), 2950, 2875, 1620 (C¼N), 1600, 1500, 1300,
1260, 1230 (C–S), 1000, 820. MS (EI, 70 eV) m/z (%):
260 (79.16) [M], 245 (100.00) [M–CH3], 213 (6.70)
[M–SCH3], 172 (28.62), 147 (12.96), 88 (29.87), 55
(29.98). HRMS calculated for C11H11F3N2S: 260.0595;
found: 260.0612.
0
0
0 0
3.3.6. 2-(4-Fluorophenylimino)-tetrahydro-thiazolidine
(3f)
2-(4-Fluorophenylimino)-tetrahydro-thiazolidine
(3f)
yield 84%, mp 153–154 8C. 1H NMR (CD3COCD3,
500 MHz) d: 3.32 (t, 2H, J ¼ 7:2 Hz, H-5), 3.92 (s, 2H,
H-4), 7.01 (m, 2H, H-30 and H-50), 7.40 (br s, 2H, H-20 and
H-60). IR (KBr) (cmꢀ1): 3125 (NH), 2800, 1630 (C¼N),
1600, 1500 (Ph), 1300, 1200, 1180, 780, 620. MS (EI, 70 eV)
m/z (%): 196 (93.04) [M], 168 (11.72) [M–CH2¼CH2], 149
(12.52) [M–SCH3], 136 (100.00) [M–C2H4S], 122 (32.36)
[M–C2H4NS], 109 (22.65) [M–C3H5NS], 95 (17.34). HRMS
calculated for C9H9 FN2S: 196.0470; found: 196.0479.
Acknowledgements
This work was supported by the National Key Project
for Basic Research (2003CB114400), Shanghai Education
Committee, National Natural Science Foundation of China,
and Ministry of Science and technology (2001AA235011).
References
3.3.7. 2-(2,3,4-Trifluorophenylimino)-tetrahydro-
thiazolidine (3g)
2-(2,3,4-Trifluorophenylimino)-tetrahydro-thiazolidine
[1] O. Ando, H. Satake, K. Itoil, A. Sato, M. Nakajima, H. Haruyama, Y.
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1
(3g) yield 80%, mp 151–152 8C. H NMR (CD3COCD3,
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[4] Y. Kobayashi, H. Miyazaki, M. Shiozaki, J. Antibiot. 47 (1994)
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500 MHz) d: 3.39 (t, 2H, J ¼ 7:0 Hz, H-5), 3.74 (t, 2H,
J ¼ 7:0 Hz, H-4), 6.90 (br s, 1H, H-60), 7.06 (q, 1H,
J4 5 ¼ 10:4 Hz, J6 5 ¼ 10:4 Hz, J3 5 ¼ 9:2 Hz, H-50). IR
(KBr) (cmꢀ1): 3150 (NH), 2850, 1650 (C¼N), 1630,
1600, 1500, 1450 (Ph), 1320, 1230, 1040, 980. MS (EI,
70 eV) m/z (%): 232 (100.00) [M], 213 (77.11) [M–F], 185
(13.55) [M–SCH3], 172 (88.86) [M–SC2H4], 158 (25.37)
[M–C2H4NS], 145 (12.94), 61 (9.61). HRMS calculated for
C9H7F3N2S: 232.0282; found: 232.0296.
0
0
0
0
0 0
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3.3.8. 2-(2,3,4-Trifluorophenylimino)-4-ethyl-4-
hydroxymethyl-thiazolidine (3h)
2-(2,3,4-Trifluorophenylimino)-4-ethyl-4-hydroxy-
methyl-thiazolidine (3h) yield 52%, mp 165–166 8C. 1H
NMR (CD3COCD3, 500 MHz) d: 1.00 (t, 3H, J ¼ 7:5 Hz,
CH3), 1.78 (q, 2H, J ¼ 7:5 Hz, CH2), 3.31 (d, 1H,
J ¼ 11:1 Hz, Ha(b)-5), 3.53 (d, 1H, J ¼ 11:1 Hz, Hb(a)-5),
3.56 (d, 1H, J ¼ 11:1 Hz, CH2a(2b)OH), 3.71 (d, 1H,
J ¼ 11:1 Hz, CH2b(2a)OH), 6.87 (br s, 0.6H, H-60), 7.05
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813–822.
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0
0
0
0
0 0
(q, 1H, J2 5 ¼ 9:1 Hz, J4 5 ¼ 10:1 Hz, J3 5 ¼ 8:4 Hz, H-
50). IR (KBr) (cmꢀ1): 3300 (OH), 3100, 2875, 1630 (C¼N),
1500 (Ph), 1250 (C–S), 1220, 1050, 980, 820. MS (EI,
70 eV) m/z (%): 290 (7.33) [M], 259 (100.00) [M–CH2OH],