Sodium hydride → HCID 15391306、化合物

HRID 1451821ノート

反応式

HRID 1451821 の反応式
[H-].[Na+].[C:3]1([C:9]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:10]2[C:14](=[O:15])[CH:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[S:12][C:11]2=[O:26])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:40]1[CH:41]=[C:42]([C:47]#[C:48][CH2:49]Br)[CH:43]=[C:44](F)[CH:45]=1.[NH4+].[Cl-:52]>CN(C=O)C.O>[C:33]1([C:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:10]2[C:14](=[O:15])[C:13]([CH2:49][C:48]#[C:47][C:42]3[CH:43]=[CH:44][C:45]([Cl:52])=[CH:40][CH:41]=3)([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[S:12][C:11]2=[O:26])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10577722HCID 10577722、化合物2 回HCID 19973049HCID 19973049、化合物

生成物 1

HCID 15391306HCID 15391306、化合物収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (80% dispersion in mineral oil, 93 mg, 3.10 mmol) was added to a solution of N-(triphenylmethyl)-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione [(VI), from Example 34, 1.06 g, 2.07 mmol) in dry DMF (9 mL) at 0° C. under a dry N2 atmosphere. After 20 min, [3-(4-chlorophenyl)-prop-2-ynyl]-bromide [(IX), from Example 21, 0.52 g, 2.27 mmol] was added and the reaction mixture was stirred an additional 20 min at 0° C. Saturated aqueous NH4Cl (60 mL) was added, followed by water (60 mL). After stirring for 10 min, the solid was filtered, washed with water and triturated with petroleum ether to provide the title compound as a grey solid (1.16 g, 90%): mp 221°-223° C.; NMR (CDCl3): δ7.80 (d, J=8.2 Hz, 2H, ArH), 7.45 (d, J=7.5 Hz, 6H, CPh3H), 7.35 (d, J=8.2 Hz, 2H, ArH), 7.14 (m, 11H, Ar'H, CPh3H), 6.98 (d, J=8.5 Hz, 2H, Ar'H), 3.29 (d, J=16.7 Hz, 1H, CH2), 3.12 (d, J=16.7 Hz, 1H, CH2), 2.46 (s, 3H, CH3).

後処理

  1. customat 0° C.
  2. stirringAfter stirring for 10 min
  3. filtrationthe solid was filtered
  4. washwashed with water
  5. customtriturated with petroleum ether

出典と根拠

ORDレコード
ord-a2a23b4fc5fe4ce0b738fbcf1f22df3e
出典データセット
uspto-grants-1997_02
特許番号
US05605918

反応ノート

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