Thioglycolic Acid → Rhodanine, 3-(4-chlorophenyl)-

HRID 1659098Notes

Reaction equation

HRID 1659098 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[SH:11][CH2:12][C:13]([OH:15])=O>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:15])[CH2:12][S:11][C:9]2=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 164804-Chlorophenyl isothiocyanate

Product 1

HCID 83070Rhodanine, 3-(4-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

A mixture of 27 g. (0.16 m.) of p-chlorophenyl isothiocyanate, 33 ml. (42.5 g., 0.475 m.) of mercaptoacetic acid and 5 drops of triethylamine is heated in a pressure bottle at 120°-130°C. for 21/2 hours. The reaction mixture is allowed to stand at room temperature overnight and filtered. The crude product is recrystallized from ethanol to give 3-(4'-chlorophenyl)-rhodanine, m.p. 124.5°-126°C.

Workup

  1. additionA mixture of 27 g
  2. filtrationfiltered
  3. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-6f77efa5d5de47a6b618e1552fdf0ab7
Source dataset
uspto-grants-1976_06
Patent number
US03966942

Reaction notes

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