Benzoyl chloride → HCID 86585975, compound

HRID 2086916Notes

Reaction equation

HRID 2086916 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]2[S:14][C:13](=[S:15])[NH:12][C:11]2=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]2[S:14][C:13](=[S:15])[N:12]([C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]2=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 27969506326-22-3

Product 1

HCID 86585975HCID 86585975, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-(3,4-dichlorophenylmethylene)-4-oxo-2-thionothiazolidine (100 mg, 0.345 mmol, 1.0equiv) was suspended in 653 μL of anhydrous pyridine, followed by the addition of 44 μL benzoyl chloride (0.379 mmol, 1.1 equiv). After about 2 minutes a yellow precipitate formed. The reaction was stirred at rt for 30 minutes. The pyridine was evaporated and the residue was purified by column chromatography (SiO2, EtOAc/hexanes) to yield 62 mg of 5-(3,4-dichlorophenylmethylene)-3-(benzoyl)-4-oxo-2-thionothiazolidine (0.157 mmol, 46%) as a yellow solid. Anal. calcd for C17H9Cl2NO2S2: C, 51.78; H, 2.30; N, 3.55; S, 16.26. Found: C, 52.04; H, 2.47; N, 3.48; S, 16.26.

Workup

  1. customAfter about 2 minutes a yellow precipitate formed
  2. customThe pyridine was evaporated
  3. customthe residue was purified by column chromatography (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-e49f571b25af42cfb069b68fecc09756
Source dataset
uspto-grants-2004_04
Patent number
US06727267B2

Reaction notes

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