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

HRID 233699Notes

Reaction equation

HRID 233699 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-af8fe88cca544134a38ddffd99f06f27
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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