Thioglycolic Acid → 4,5-Diphenyl-2-oxazolyl mercaptoacetic acid

HRID 2072544

Reaction equation

HRID 2072544 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].C[O-].[Na+].Cl[C:10]1[O:11][C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1>C1COCC1>[C:15]1([C:13]2[N:14]=[C:10]([CH:2]([SH:3])[C:1]([OH:5])=[O:4])[O:11][C:12]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 10942334Sodium MethoxideHCID 131311622-Chloro-4,5-diphenyloxazole

Product 1

HCID 214083604,5-Diphenyl-2-oxazolyl mercaptoacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.15 g. of the cyclohexyl ester of thioglycolic acid is dissolved in 80 ml. of absolute THF, and 2.6 g. of sodium methylate is added thereto. The reaction mixture is agitated for 15 minutes. Then, 12 g. of 2-chloro-4,5 -diphenyl-oxazole (b.p. 170°/0.05 mm.; producible by reacting 4,5-diphenyl-2-oxazolone with POCl3) in 20 ml. of THF is added dropwise. The reaction mixture is refluxed under agitation for 9 hours. The thus-precipitated NaCl is filtered off and the filtrate concentrated by evaporation, thus obtaining the cyclohexyl ester of 4,5-diphenyl-2-oxazolyl mercaptoacetic acid as an oily residue. The latter (16 g.) is refluxed in 150 ml. of ethanol with 8 g. of pulverized K2CO3 for 2 hours. After conducting the usual working-up operation, 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid is obtained, m.p. 137°-138°.

Workup

  1. temperatureThe reaction mixture is refluxed under agitation for 9 hours
  2. filtrationThe thus-precipitated NaCl is filtered off
  3. concentrationthe filtrate concentrated by evaporation

Sources & evidence

ORD record
ord-d661b4a125a144258855ea68bf31f0be
Source dataset
uspto-grants-1977_09
Patent number
US04051250

Linked notes

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