Hydrochloric Acid → HCID 21557622, compound

HRID 1579062Notes

Reaction equation

HRID 1579062 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][S:13][C:14]=2[C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1.[CH2:18]([CH:20]1[O:22][CH2:21]1)Br.Cl>O>[O:22]1[CH2:21][CH:20]1[CH2:18][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][S:13][C:14]=2[C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18430EpibromohydrinHCID 21557684HCID 21557684, compound

Product 1

HCID 21557622HCID 21557622, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 80 mg. of sodium hydroxide in 10 ml. of water is added 250 mg. of 4-(4-hydroxyphenyl)-5-carboxy-1,2,3-thiadiazole. The reaction mixture is stirred for 10 minutes and then treated dropwise with 0.4 ml. of epibromohydrin, maintaining the reaction mixture at room temperature under stirring for 48 additional hours. It is then acidified with 10% hydrochloric acid solution and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate and evaporated to dryness under reduced pressure. Crystallization of the residue from chloroformmethanol affords the pure 4-[4(2,3-epoxypropoxy)phenyl]-5-carboxy-1,2,3-thiadiazole.

Workup

  1. additiontreated dropwise with 0.4 ml
  2. stirringunder stirring for 48 additional hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customCrystallization of the residue from chloroformmethanol

Sources & evidence

ORD record
ord-8c6103a13afe416492b890f0a09385d2
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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