Formaldehyde → HCID 13853382, compound

HRID 978306Notes

Reaction equation

HRID 978306 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C=O.[SH:15][CH2:16][C:17]([OH:19])=O.[C:20]1(C)C(C)=CC=CC=1>O>[O:19]=[C:17]1[CH2:16][S:15][CH2:20][N:1]1[C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1133Thioglycolic AcidHCID 2337BenzocaineHCID 7237O-Xylene

Product 1

HCID 13853382HCID 13853382, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl p-aminobenzoate (7.3 g) was reacted with 37% formalin (formaldehyde in water) (3.2 ml), mercaptoacetic acid (3.0 ml) and xylene (300 ml). This reaction mixture was refluxed and the water formed thereby was removed azeotropically. After all the water was removed, xylene was evaporated under reduced pressure and the residual oil taken up in methylene chloride. Removal of the methylene chloride solvent left an orange solid which was recrystallized from ethanol to give ethyl 4-(4-oxo-3-thiazolidinyl)benzoate. This product had a melting point of 68°-69° C.

Workup

  1. temperatureThis reaction mixture was refluxed
  2. customthereby was removed azeotropically
  3. customAfter all the water was removed
  4. customxylene was evaporated under reduced pressure
  5. customRemoval of the methylene chloride solvent
  6. waitleft an orange solid which
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-451403b1d9294175adc3d9a8587ff1ec
Source dataset
uspto-grants-1987_05
Patent number
US04664694

Reaction notes

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