Thioglycolic Acid → HCID 408483, compound

HRID 2232566Notes

Reaction equation

HRID 2232566 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.[C:18]([OH:22])(=[O:21])[CH2:19][SH:20]>N1C=CC=CC=1>[C:12]1([C:4]2[CH:3]=[C:2]([S:20][CH2:19][C:18]([OH:22])=[O:21])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 2783764-chloro-2-phenylquinoline

Product 1

HCID 408483HCID 408483, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chloro-2-phenylquinoline (3 g) and thioglycolic acid (1.38 g) in pyridine (40 cc) are heated under reflux for 4 hours. After evaporation of the pyridine under reduced pressure, the residue is taken up with water (125 cc) and normal aqueous sodium hydroxide solution (40 cc). The aqueous phase is washed with ethyl ether (2×50 cc), acidified to pH 5 with glacial acetic acid and extracted with ethyl ether (3×50 cc). The ether phase is washed with water, dried over magnesium sulphate an evaporated under reduced pressure. [(2-Phenyl-4-quinolyl)thio]acetic acid (3.2 g), m.p. 138° C., is thereby obtained.

Workup

  1. temperatureunder reflux for 4 hours
  2. customAfter evaporation of the pyridine under reduced pressure
  3. washThe aqueous phase is washed with ethyl ether (2×50 cc)
  4. extractionextracted with ethyl ether (3×50 cc)
  5. washThe ether phase is washed with water
  6. dry with materialdried over magnesium sulphate
  7. customan evaporated under reduced pressure

Sources & evidence

ORD record
ord-f4470cbd2cdd42e3a639c7e4c487c372
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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