Toluene → 3-(2-Benzothiazolyl)-5-(phenylmethyl)-2-thioxo-4-thiazolidinone

HRID 861594Notes

Reaction equation

HRID 861594 reaction equation
COC(=O)C(CC1C=CC=CC=1)N[C:6]([NH:8][C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)=[S:7].[OH2:26].C1(C)C=C[C:30]([S:33](O)(=O)=O)=[CH:29]C=1.[C:38]1([CH3:44])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[S:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[N:8]1[C:29](=[O:26])[CH:30]([CH2:44][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[S:33][C:6]1=[S:7]

Participants

4

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 19703398N-[(2-benzothiazolylamino)thioxomethyl]-DL-phenylalanine methyl ester

Product 1

HCID 197041613-(2-Benzothiazolyl)-5-(phenylmethyl)-2-thioxo-4-thiazolidinoneYield 8%

Procedure

A solution of N-[(2-benzothiazolylamino)thioxomethyl]-DL-phenylalanine methyl ester (1.0 g, 2.69 mmol) and p-toluene sulfonic acid hydrate (0.20 g 1.05 mmol) in toluene (80 mL) was refluxed with a Dean-Stark trap for 36 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, residue taken up in ethyl acetate, washed with saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting product was recrystallized from ethyl acetate-hexanes to provide 74.9 mg (8%) of the titled product:

Workup

  1. customsolvent removed under reduced pressure, residue
  2. washwashed with saturated sodium bicarbonate and saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting product was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-53c1f812d4514fde9d7de93c6e945d78
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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