Sodium Hydroxide → 2-(4,5-Diphenyl-1,3-oxazol-2-ylthio)acetic acid

HRID 1414203Notes

Reaction equation

HRID 1414203 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][C:20]([O:22]CC)=[O:21])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][C:20]([OH:22])=[O:21])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 776821Ethyl [(4,5-diphenyl-1,3-oxazol-2-yl)thio]acetate

Product 1

HCID 7224662-(4,5-Diphenyl-1,3-oxazol-2-ylthio)acetic acidYield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g ethyl S-(4,5-diphenyloxazol-2-yl)-mercaptoacetate dissolved in 30 ml ethanol were mixed with 30 ml 40% NaOH and maintained for 1 hour at room temperature. The sodium salt which separated from the reaction mixture was redissolved by means of addition of 200 ml distilled water. The alkaline solution was slowly poured into 300 ml ice-cooled 15% HCl. The precipitated S-(4,5-diphenyloxazol-2-yl)-mercaptoacetic acid was filtered, washed with water and crystallized from aqueous ethanol to give 7.4 g of a product melting at 137°-139° C (yield = 80.7%).

Workup

  1. customThe sodium salt which separated from the reaction mixture
  2. dissolutionwas redissolved by means of addition of 200 ml
  3. distillationdistilled water
  4. additionThe alkaline solution was slowly poured into 300 ml ice-
  5. temperaturecooled 15% HCl
  6. filtrationThe precipitated S-(4,5-diphenyloxazol-2-yl)-mercaptoacetic acid was filtered
  7. washwashed with water
  8. customcrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-45b85c4d28754cbc80645a33f51066ed
Source dataset
uspto-grants-1977_01
Patent number
US04001228

Reaction notes

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