Formaldehyde → 3-(3-Bromo-4-chlorophenyl)thiazolidin-4-one

HRID 377021Notes

Reaction equation

HRID 377021 reaction equation
[C:1]([OH:5])(=O)[CH2:2][SH:3].[CH2:6]=O.[Br:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[Cl:16])[NH2:12]>C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:10]=[C:11]([N:12]2[C:1](=[O:5])[CH2:2][S:3][CH2:6]2)[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1133Thioglycolic AcidHCID 128437223-Bromo-4-chloroaniline

Product 1

HCID 193607783-(3-Bromo-4-chlorophenyl)thiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thioglycolic acid (8.65 g) and 37% aqueous formaldehyde (4.6 ml) was added to a stirred solution of 3-bromo-4-chloroaniline (9.73 g) in toluene (50 ml). The mixture was heated to reflux and the water collected in a Dean and Stark apparatus. After 3 hours the mixture was cooled, diluted with toluene then washed with aqueous sodium hydroxide and water. The organic layer was dried (MgSO4) and concentrated to give the subtitle compound as a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customthe water collected in a Dean and Stark apparatus
  4. temperatureAfter 3 hours the mixture was cooled
  5. additiondiluted with toluene
  6. washthen washed with aqueous sodium hydroxide and water
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-55f5dd449ef5494aac677a1f07786f7f
Source dataset
uspto-grants-2000_02
Patent number
US06022976

Reaction notes

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