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

HRID 1899882ノート

反応式

HRID 1899882 の反応式
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

参加物

5

反応物 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 15391306HCID 15391306、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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): δ 8.00 (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.

後処理

  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

出典と根拠

ORDレコード
ord-9ea6033519744594a1ff5f1273a1ea2b
出典データセット
uspto-grants-1996_11
特許番号
US05574051

反応ノート

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