Formaldehyde → HCID 13853377, compound

HRID 978308Notes

Reaction equation

HRID 978308 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[SH:10][CH:11]([CH2:15][C:16]([OH:18])=[O:17])[C:12](O)=[O:13].[CH2:19]=O.O>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]2[C:12](=[O:13])[CH:11]([CH2:15][C:16]([OH:18])=[O:17])[S:10][CH2:19]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 6268(+-)-Mercaptosuccinic acidHCID 72573,4-Dichloroaniline

Product 1

HCID 13853377HCID 13853377, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3,4-Dichloroaniline (16.2 g, 0.1 mol) and mercaptosuccinic acid (15 g) were dissolved in xylene (200 ml). While stirring, 37% formalin (8.5 ml) was added followed by heating to reflux. The water formed (9 ml) during this reaction was removed azeotropically. The reaction mixture was filtered hot, befored removing the solvent, to leave an oil, 3-(3,4-dichlorophenyl)-4-oxo-5-thiazolidineacetic acid, which solidified. This crude product was esterified in isopropyl alcohol (500 ml) and concentrated sulfuric acid (3 ml). Removal of the solvent left a crude product which was taken up in methylene chloride, washed with water, dried and evaporated. Recrystallization of the product from toluene/ligroin gave 1-methylethyl 3-(3,4-dichlorophenyl)-4-oxo-5-thiazolidineacetate which had a melting point of 54°-56° C.

Workup

  1. temperatureby heating to reflux
  2. customwas removed azeotropically
  3. filtrationThe reaction mixture was filtered hot
  4. custombefored removing the solvent

Sources & evidence

ORD record
ord-9c4d3541637a498398247c8f188b9974
Source dataset
uspto-grants-1987_05
Patent number
US04664694

Reaction notes

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