Catalytic Hydrogenation of Halothiazoles

References

• Erlenmeyer , H. and Morel , C. J. 1945 . Helv. Chim. Acta , 28 : 362
   Google Scholar
• Erlenmeyer , H. and Kiefer , H. 1945 . Helv. Chim. Acta , 28 : 985
   Google Scholar
• Athmani , S. , Bruce , A. and Iddon , B. 1992 . J. Chem. Soc. Perkin Trans. , 1 : 215 and references contained therein
   Google Scholar
• Dondoni , A. , Fantin , G. , Fogagnolo , M. and Medici , A. 1988 . J. Org. Chem. , 53 : 1748 and references contained therein
   Web of Science ®Google Scholar
• Begtrup , M. and Hansen , L. 1992 . Acta Chem. Scand. , 46 : 372
   Google Scholar
• Kato , S. and Ishizaki , M. JP 63250385 A2 881018 . 1988 .
   Google Scholar
• Sakamoto , T. , Nagata , H. , Kondo , Y. , Shiraiwa , M. and Yamanaka , H. 1987 . Chem. Pharm. Bull. , 35 : 823
   Google Scholar
• Ahluwalia , V. K. , Arora , K. K. , Kaur , G. and Mehta , B. 1987 . Synth. Commun. , 17 : 330
   Google Scholar
• Robba , M. and Moreau , R. C. 1964 . Ann. Pharm. Fr. , 22 : 201 The starting materials were prepared as follows: entry 1
   PubMedGoogle Scholar
• Roussel , P. and Metzger , J. 1962 . Bull. Soc. Chim. Fr. , : 2075 entry 2
   Google Scholar
• Beck , G. Patent U. S. 4,555,577 . 1985 . entry 3, see ref. 3a (d) entry 4
   Google Scholar
• Kerdesky , F. A.J. and Seif , L. S. Synth. Commun. , entries 5 and 6 in press
   Google Scholar
• Spectral and physical data of all the compounds cited in Table I are as follows: (a) Thiazole: bp 117–118°C (lit. 4a 117°C); 1H NMR (300 MHz, CDCl3): δ 8.84 (s, 1H), 7.97 (d, 1H), 7.41 (m, 1H); MS (DCl/NH3) m/e 86 (M+H)+. (b) 5-Thiazolecarboxaldehyde: bp 92–94°C at 12 mm Hg (lit. 9 90–94°C at 12 mm Hg); 1H NMR (300 MHz, CDCl3): δ 10.10 (s, 1H), 9.11 (s, 1H), 8.52 (s, 1H); MS (DCl/NH3) m/e 114 (M+H)+. (c) 5-(Hydroxymethyl)thiazole: bp 140–142°C at 10 mm Hg (lit. 10 bp 133–140°C at 10 mm Hg), 1H NMR (300 MHz, CDCl3): δ 8.80 (s, 1H), 7.80 (s, 1H), 4.92 (s, 2H), 2.12 (brs, 1H); MS (DCl/NH3) m/e 116 (M+H)+. (d) 4-Bromothiazole: bp 189–190°C (lit. 4a 189–190°C); 1H NMR (300 MHz, CCl4): δ 8.70 (s, 1H), 7.24 (s, 1H); MS (DCl/NH3) m/e 165 (M+H)+. (e) 2,5-Dibromothiazole: mp 46–47°C (lit. 4b 46–47°C); 1H NMR (300 MHz, CDCl3): δ 7.45 (s, 1H); MS (DCl/NH3) m/e 245 (M+H)+. (f) 2,4-Dibromo-5-thiazolecarboxaldehyde: mp 80–81°C (lit. 3a mp 80–81°C); 1H NMR (300 MHz, CDCl3): δ 9.89 (s, 1H); MS (DCl/NH3) m/e 272 (M+H)+. (g) 2,4-Dichloro-5-thiazolecarboxaldehyde: mp 48–49°C (lit. 4d mp 48–49°C); 1H NMR (300 MHz, CDCl3): δ 9.96 (s, 1H); MS (DCl/NH3) m/e 182 (M+H)+. (h) 2,4-Dibromo-5-(hydroxymethyl)thiazole: mp 87–88°C (lit. 4e mp 87–88°C); 1H NMR (300 MHz, CDCl3): δ 4.79 (d, 2H), 2.18 (t, 1H); MS (DCl/NH3) m/e 274 (M + H)+. (i) 2,4-Dichloro-5-(hydroxymethyl)thiazole: mp 53–54°C (lit. 46 mp 53–54°C); 1H NMR (300 MHz, CDCl3): δ 4.81 (d, 2H), 2.24 (t, 1H); MS (DCl/NH3) m/e 184 (M+H)+
   Google Scholar
• Wilson , J. R.H. and Sawhney , I. U. S. Patent 5,089,512 . 1992 .
   Google Scholar
• Kempt , D. J. , Codacovi , L. M. , Norbeck , D. W. , Plattner , J. J. , Sham , H. L. , Wittenberger , S. J. and Zhao , C. Eur. Pat. Appl. EP-486948 A2 920527 . 1992 .
   Google Scholar
• 1H NMR (300 MHz, CDCl3): δ 8.70 (s, 1H), 4.88 (d, 2H), 2.02 (t, 1H); MS (DCl/NH3) m/e 150 (M+H)+. Anal. Calcd for C4H4ClNOS: C, 32.11; H, 2.69; N, 9.36. Found: C, 31.99; H, 2.67; N, 9.40
   Google Scholar
• Dorlars , A. Ger Patent 1, 182,234 . 1964 .
   Google Scholar