Water → 2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

To the aqueous phase from Example 14 above was added 27 g. of 2-aminoethanethiol, hydrochloride. The mixture was heated and stirred, until the pot temperature reached 120°. The mixture was held at that temperature for 6 hours, and was then allowed to cool to 60°. To the residue was added 80 ml. of deionized water, and the mixture was allowed to cool to ambient temperature and stand for some days. Eighty ml. of dichloromethane was then added, and the pH of the mixture was adjusted to 6.1 by the addition of 9 ml. of 50% sodium hydroxide. The aqueous layer was extracted twice with 40 ml. portions of dichloromethane, and the aqueous layer was then mixed with 80 ml. of dichloromethane and the pH was adjusted to 12.6 by the addition of 40 ml. of 50% sodium hydroxide. The aqueous layer of the resulting mixture was extracted twice with 40 ml. of dichloromethane, and the two aqueous layers were combined, filtered and evaporated under vacuum to obtain 31.5 g. of the desired product, which was found to be 74.7% pure by the analytical method described in Preparation 1 above.

1. temperatureThe mixture was heated
2. customreached 120°
3. temperatureto cool to 60°
4. additionTo the residue was added 80 ml
5. waitstand for some days
6. additionthe pH of the mixture was adjusted to 6.1 by the addition of 9 ml
7. extractionThe aqueous layer was extracted twice with 40 ml
8. additionportions of dichloromethane, and the aqueous layer was then mixed with 80 ml
9. additionof dichloromethane and the pH was adjusted to 12.6 by the addition of 40 ml
10. extractionThe aqueous layer of the resulting mixture was extracted twice with 40 ml
11. filtrationfiltered
12. customevaporated under vacuum
13. customto obtain 31.5 g

ORD record

ord-9a348502f595434ca75088b29493b1a4

Source dataset

uspto-grants-1984_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04468517