Thioglycolic Acid → 3-(3,4-Dichlorophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one

HRID 1659109Notes

Reaction equation

HRID 1659109 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[SH:12][CH2:13][C:14]([OH:16])=O>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:16])[CH2:13][S:12][C:10]2=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 230651,2-Dichloro-4-isothiocyanatobenzene

Product 1

HCID 994663-(3,4-Dichlorophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

A mixture of 6.12 g. (0.03 m.) of 3,4-dichlorophenyl isothiocyanate, 2.8 ml. (3.68 g., 0.04 m.) of mercaptoacetic acid and a few drops of triethylamine is heated in a pressure bottle at 110°-130°C. for 2 hours. The cooled reaction mixture is filtered to give 3-(3',4'-dichlorophenyl)-rhodanine, m.p. 176°-178°C.

Workup

  1. additionA mixture of 6.12 g
  2. customThe cooled reaction mixture
  3. filtrationis filtered

Sources & evidence

ORD record
ord-9e441cbd89344df19947564bea600069
Source dataset
uspto-grants-1976_06
Patent number
US03966942

Reaction notes

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