3,4-Dichlorophenol → HCID 85055384, compound

HRID 1058638Notes

Reaction equation

HRID 1058638 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1)([OH:3])=[O:2].[Cl:18][C:19]1[CH:20]=[C:21](O)[CH:22]=[CH:23][C:24]=1[Cl:25].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:24]=1[Cl:25])[O:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[C:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:16][CH:17]=1)=[O:3]

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 5003267HCID 5003267, compound

Product 1

HCID 85055384HCID 85055384, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Carboxybenzylidene)thiazolidine-2,4-dione (from Example 8, Step A) was dissolved in SO2Cl2 followed by addition of 1-2 drops of DMF. This resulting mixture was heated to ˜80° C. for 15-30 min at which time the reaction was concentrated under reduced pressure. The residue was dissolved in THF and added drop wise to a solution of 3,4-dichlorophenol (1.5 eq) and TEA (2 eq). This resulting mixture was stirred for additional 1-2 h at which time the solid in the reaction mixture was filtered off. The filtrate was concentrated under reduced pressure to yield solid that was washed with water and ether to afford pure ester. Alternatively, to a solution of 5-(4-carboxybenzylidene)thiazolidine-2,4-dione (1 eq) and 3,4-dichlorophenol (1 eq) in CH2Cl2 was added DCC (1 eq). The resulting reaction mixture was stirred for 16 h at which time the reaction was filtered, the filtrate was washed with water and concentrated under reduced pressure to provide crude product that was purified by recystallization.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered
  3. washthe filtrate was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customto provide crude product that
  6. customwas purified by recystallization

Sources & evidence

ORD record
ord-89ab33a39d7845f7ad1123a70ec938cb
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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