Sodium hydride → HCID 15391306, 화합물

HRID 1451821노트

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HRID 1451821 반응식
[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

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10577722HCID 10577722, 화합물2회HCID 19973049HCID 19973049, 화합물

생성물 1

HCID 15391306HCID 15391306, 화합물수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a2a23b4fc5fe4ce0b738fbcf1f22df3e
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05605918

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