How to prepare 5-Hydroxymethylthiazole

5-Hydroxymethylthiazole is a kind of slightly yellow oil liquids, the Molecular Formula is C4H5NOS, Molecular weight is 115.15, and the CAS NO. is 38585-74-9. It is an important intermediate for Ritonavir, and a kind of anti-AIDS pharmaceuticals. But how to prepare it, now I will give you 4 examples.

Example 1:

In a reaction flask IOml 50ml of methanol, 1. 5g (IOmmol) 2_ chloro-5 - (hydroxymethyl) thiazole and 1. 7g (26mmol) of zinc powder, the above mixture was heated to 50 C, and hydrochloric acid was slowly added 30ml (IN), at a temperature of 60 C for 2 hours detected by TLC or HPLC, until the starting material disappeared, the reaction was stopped and the reaction solution was filtered, concentrated and neutralized with sodium hydroxide to PH is 9, then extracted with ethyl acetate to give crude product, the final crude solvent was removed by distillation under reduced pressure, collecting 115 ~ 122 C (24mmHg) the distillate, 1.05g 5 - (hydroxymethyl) thiazole. The determination of the purity of 94%, the yield was 85%.

Example 2:

In a reaction flask IOOml 250ml of ethanol, 15g (0. Imol) 2_ chloro-5 - (hydroxymethyl) thiazole and 13. 5g (0. 20mol) zinc powder, the above mixture was heated to 50 C , then slowly add 150ml hydrochloric acid (2N), at a temperature of 70 C for 2 hours detected by TLC or HPLC, until the starting material disappeared, the reaction was stopped and the reaction solution was filtered, concentrated and neutralized with sodium hydroxide to PH of 10, and then extracted with ethyl acetate to give crude product, the final crude solvent was removed by distillation under reduced pressure, collecting 115 ~ 122 C (24mmHg) the distillate, 8. 5g 5 - (hydroxymethyl) thiazole. The determination of the purity% 99. 3% (HPLC), the yield was 74%.

Example 3:

In a reaction flask 50ml IOml propanol, 1. 5g (IOmmol) 2_ chloro-5 - (hydroxymethyl) thiazole and 0. 95g (15mmol) of zinc powder, the above mixture was heated to 50 C , then slowly add 3ml of sulfuric acid (6N), at a temperature of 40 C for 5 hours, TLC or HPLC detection, until the starting material disappeared, the reaction was stopped and the reaction solution was filtered, concentrated and neutralized with sodium hydroxide to PH is 9, then extracted with ethyl acetate to give crude product, the final crude solvent was removed by distillation under reduced pressure, collecting 115 ~ 122 C (24mmHg) fraction, to l.lg 5 - (hydroxymethyl) thiazole. The determination of the purity of 91%, the yield was 95%.

Example 4:

In a reaction flask IOOml 250ml of ethanol, 45g (0. 3mol) 2_ chloro-5 - (hydroxymethyl) thiazole and 33g (0. 5mol) zinc powder, and then added slowly 75ml hydrochloric acid (6N), the temperature of 60 C for 2 hours, by TLC or HPLC detection, until the starting material disappeared, the reaction was stopped and the reaction solution was filtered, concentrated and neutralized with sodium hydroxide to a PH of 10, and then extracted with ethyl acetate and to give the crude product, the final crude solvent was removed by distillation under reduced pressure, collecting 115 ~ 1220C (24mmHg) the distillate, 25g 5 - (hydroxymethyl) thiazole. The purity was determined 99. 5% (HPLC), the yield was 72%.

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