Acetic Acid → HCID 13853375, compound

HRID 978305Notes

Reaction equation

HRID 978305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[C:10]([OH:14])(=O)[CH2:11][SH:12].C=O.[C:17](O)(=O)C>C(O)C.C1(C)C(C)=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]2[C:10](=[O:14])[CH2:11][S:12][CH2:17]2)[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 1133Thioglycolic AcidHCID 122813,5-Dichloroaniline

Product 1

HCID 13853375HCID 13853375, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

3,5-Dichloroaniline (40.25 g, 0.25 mol) and thioglycolic acid (23 g, 0.25 mol) in ethanol (75 ml) were mixed and stirred. Formaldehyde solution (21.3 ml, 37% by weight) was added to the solution. An exotherm developed and a solid precipitated out. After stirring for several hours, water was added. The solids that had precipitated were collected on a filter, washed with water and air-dried. The product, 2-[[(3,5-dichlorophenyl)amino]methyl]thio]acetic acid (38 g, 0.15 mol), was refluxed in xylene (275 ml). The water formed during refluxing was removed azeotropically. Removal of the solvent left a solid having a melting point of 87°-92° C.

Workup

  1. customa solid precipitated out
  2. stirringAfter stirring for several hours
  3. additionwater was added
  4. customThe solids that had precipitated
  5. customwere collected on a filter
  6. washwashed with water
  7. customair-dried
  8. temperatureduring refluxing
  9. customwas removed azeotropically
  10. customRemoval of the solvent
  11. waitleft a solid

Sources & evidence

ORD record
ord-de9dfc0dedb6425db9a55e11ae15e3d2
Source dataset
uspto-grants-1987_05
Patent number
US04664694

Reaction notes

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