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

HRID 1580806

Reaction equation

HRID 1580806 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-a3af9fe1d3454831988a96387a96a0e4
Source dataset
uspto-grants-1976_01
Patent number
US03933840

Linked notes

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