Sodium Hydroxide → 4-[4-(Oxiran-2-ylmethoxy)phenyl]-1,2,3-thiadiazole

HRID 1579050

Reaction equation

HRID 1579050 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][S:13][CH:14]=2)=[CH:6][CH:5]=1.[CH2:15]([CH:17]1[O:19][CH2:18]1)Br>O>[O:19]1[CH2:18][CH:17]1[CH2:15][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[N:12][S:13][CH:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18430EpibromohydrinHCID 27968604-(1,2,3-Thiadiazol-4-Yl)Phenol

Product 1

HCID 27371034-[4-(Oxiran-2-ylmethoxy)phenyl]-1,2,3-thiadiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. stirringThe reaction mixture is stirred for 48 hours
  2. extractionextracted several times with ethyl acetate
  3. washThe combined organic extracts are washed with water to neutrality
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under vacuo
  6. customThe semisolid residue is crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-f391237350f5492a937ff261322763b3
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Linked notes

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