تفاعل #1687639

ord-89faf8cefd0b4a368e653361d4563732

معادلة التفاعل

CCSCCO
2-(ethylthio) ethanol
CS(=O)(=O)O
MeSO3H
CCSCCOc1nsnc1-c1cccnc1
3-(4-(2-ethylthio-1-ethoxy)- 1,2,5-thiadiazol-3-yl)pyridine
[Na+].[OH-]
NaOH
O
water
CCS(=O)CCOc1nsnc1C1=CCCN(C)C1.O=C(O)C(=O)O
1,2,5,6-tetrahydro-1-methyl-3-(3-(2-ethylsulfinyl-1-ethoxy)- 1,2,5-thiadiazol-4-yl)pyridine oxalate

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىAfter a reaction time of 3.5 h.
  2. 2
    استخلاصextracted with ethyl acetate
  3. 3
    تجفيفThe combined extracts were dried over MgSO4
  4. 4
    أخرىevaporated under vacuum

الإجراء التجريبي

1,2,5,6-tetrahydro-1-methyl-3-(3-(2-ethylsulfinyl-1-ethoxy)- 1,2,5-thiadiazol-4-yl)pyridine oxalate was prepared in the same manner using 2-(ethylthio) ethanol as the starting alcohol. The intermediate 3-(4-(2-ethylthio-1-ethoxy)- 1,2,5-thiadiazol-3-yl)pyridine was oxidized with 1.1 equivalent of NaIO4 and 1 equivalent MeSO3H using water as the reaction solvent. After a reaction time of 3.5 h. the solution was made basic with 2N NaOH and extracted with ethyl acetate. The combined extracts were dried over MgSO4 and evaporated under vacuum. The resulting sulfoxide was then converted to the title compound in the same manner described above. M.p. 171°-172° C., M+ : 302. Compound 45.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: USRE036375uspto-grants-1999_11