Sodium Hydroxide → HCID 21557787, compound

HRID 1579056Notes

Reaction equation

HRID 1579056 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][N:13]=[N:12][CH:11]=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[S:14][N:13]=[N:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18430EpibromohydrinHCID 135819062HCID 135819062, compound

Product 1

HCID 21557787HCID 21557787, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.92 g. of sodium hydroxide in 425 ml. of water is added 4.1 g. of 5-(4-hydroxyphenyl)-1,2,3-thiadiazole and 5.4 ml. of epibromohydrin, stirring the reaction mixture for 20 hours at room temperature. It is then extracted with ethyl acetate, and the organic extract washed with water to neutrality, dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue is chromatographed on silica gel plates using a mixture of chloroform-acetone (95:5) as eluant to yield 5-[4(2,3-epoxypropoxy)phenyl]-1,2,3-thiadiazole. This product can be further purified by crystallization from methylene chloridehexane.

Workup

  1. extractionIt is then extracted with ethyl acetate
  2. extractionthe organic extract
  3. washwashed with water to neutrality
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is chromatographed on silica gel plates
  7. additiona mixture of chloroform-acetone (95:5) as eluant

Sources & evidence

ORD record
ord-60b4e2100d3a4917b152faa47174e85d
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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