Water → 5-[3-(4-Chlorophenyl)-prop-2-ynyl]-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione

HRID 1451822Notes

Reaction equation

HRID 1451822 reaction equation
FC(F)(F)C(O)=O.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:15]2[C:19](=[O:20])[C:18]([CH2:31][C:32]#[C:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[S:17][C:16]2=[O:41])C=CC=CC=1.O>C(Cl)Cl>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C:33]#[C:32][CH2:31][C:18]2([S:21]([C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)(=[O:22])=[O:23])[S:17][C:16](=[O:41])[NH:15][C:19]2=[O:20])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 15391306HCID 15391306, compound

Product 1

HCID 107645705-[3-(4-Chlorophenyl)-prop-2-ynyl]-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.32 mL, 4.07 mmol) was added to a room temperature, stirred suspension of N-(triphenylmethyl)-5-[3-(4-chlorophenyl)-prop-2-ynyl]-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione [(X), from Example 35, 1.29 g, 1.94 mmol] in CH2Cl2 (2 mL). Dissolution occurred immediately. After 1 h, the reaction mixture was added to water (200 mL) and extracted with ethyl acetate (200 mL). The ethyl acetate phase was washed with water and brine and then concentrated. The crude product was purified by flash chromatography (95:5 CH2Cl2 :isopropanol) and then triturated in petroleum ether to provide the title compound as a off-white solid (0.52 g, 64%): mp 172°-174° C.; NMR (CDCl3): δ8.00 (s, 1H, NH) 7.85 (d, J=8.3 Hz, 2H, ArH), 7.41 (d, J=8.3 Hz, 2H, ArH), 7.26 (s, 4H, Ar'H), 3.65 (d, J=17.1 Hz, 1H, CH2), 3.33 (d, J=17.1 Hz, 1H, CH2), 2.49 (s, 3H, CH3); MS(CI); 420 (M+H, 58%), 422 (M+H, 24%), 265 (40%), 267 (26%),157 (100%); Anal. Calc. for C19H14ClNO4S2 : C, 54.35; H, 3.36; N, 3.36; Found: C, 54.74; H, 3.54; N, 2.98.

Workup

  1. dissolutionDissolution
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe ethyl acetate phase was washed with water and brine
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (95:5 CH2Cl2 :isopropanol)
  6. customtriturated in petroleum ether

Sources & evidence

ORD record
ord-7a2feea265b14682bb4b54b09e73f427
Source dataset
uspto-grants-1997_02
Patent number
US05605918

Reaction notes

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