ChemicalBook CAS DataBase List 4-[4-(OXIRAN-2-YLMETHOXY)PHENYL]-1,2,3-THIADIAZOLE

4-[4-(OXIRAN-2-YLMETHOXY)PHENYL]-1,2,3-THIADIAZOLE synthesis

4synthesis methods

Product Name:4-[4-(OXIRAN-2-YLMETHOXY)PHENYL]-1,2,3-THIADIAZOLE
CAS Number:59834-07-0
Molecular formula:C11H10N2O2S
Molecular Weight:234.27

59834-05-8 Synthesis

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4-[4-(OXIRAN-2-YLMETHOXY)PHENYL]-1,2,3-THIADIAZOLE

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Yield:-

Reaction Conditions:

with sodium hydroxide in water;

Steps:

4 EXAMPLE 4

EXAMPLE 4 To a solution of 0.112 g. of sodium hydroxide in 10 ml. of water is added 0.499 g. of 4-(4-hydroxyphenyl)1,2,3-thiadiazole and to the resulting solution is added dropwise, under stirring, 0.66 ml. of epibromohydrin, in a 5 minute period. The reaction mixture is stirred for 48 hours and extracted several times with ethyl acetate. The combined organic extracts are washed with water to neutrality, dried over anhydrous sodium sulfate and evaporated to dryness under vacuo. The semisolid residue is crystallized from methylene chloride-hexane to yield the pure 4-[4(2,3-epoxypropoxy)phenyl] 1,2,3-thiadiazole. In a similar manner, the remaining compounds obtained in Example 3 are converted respectively into: 4-[2(2,3-epoxypropoxy)phenyl] -1,2,3-thiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-1,2,3-thiadiazole, 4-[2(2,3-epoxypropoxy)phenyl]-5-methyl-1,2,3-thiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-5-methyl-1,2,3-thiadiazole, 4-[4(2,3-epoxypropoxy)phenyl]-5-methyl-1,2,3-thiadiazole, 4-[2(2,3-epoxypropoxy)phenyl]-5-ethyl-1,2,3-thiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-5-ethyl-1,2,3-thiadiazole, 4-[2(2,3-epoxypropoxy)phenyl]-5-propyl-1,2,3-thiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-5-propyl-1,2,3-thiadiazole, 4-[4(2,3-epoxypropoxy)phenyl]-5-propyl-1,2,3-thiadiazole, 4-[2(2,3-epoxypropoxy)phenyl]-5-cyano-1,2,3-thiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-5-cyano-1,2,3-thiadiazole, 4-[4(2,3-epoxypropoxy)phenyl]-5-cyano-1,2,3-thiadiazole, 4-[2(2,3-epoxypropoxy)phenyl]-5-trifluoromethyl-1,2,3-tiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-5-trifluoromethyl-1,2,3-thiadiazole, 4-[4(2,3-epoxypropoxy)phenyl]-5-trifluoromethyl-1,2,3-thiadiazole, 4-[2(2,3-epoxypropoxy)phenyl]-5-phenyl-1,2,3-thiadiazole, 4-[4(2,3-epoxypropoxy)phenyl]-5-phenyl-1,2,3-thiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-5-phenyl-1,2,3-thiadiazole, 4-[2(2,3-epoxypropoxy)phenyl]-5-carboethoxy-1,2,3-thiadiazole, 4-[3(2,3-epoxypropoxy)phenyl]-5-carboethoxy-1,2,3-thiadiazole and 4-[4(2,3-epoxypropoxy)phenyl]-5-carboethoxy-1,2,3-thiadiazole.

References:

US3940407,1976,A