p-Chlorothiophenol → HCID 67597008、化合物

HRID 1490306ノート

反応式

HRID 1490306 の反応式
FC(F)(F)S(O)(=O)=O.[Cl:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[C:12]2[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[O:23][C:11]1=2.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([SH:35])=[CH:31][CH:30]=1>C(OCCO)C.CCCCCC>[Cl-:9].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N+:13]([CH3:20])=[C:12]3[C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[O:23][C:11]=23)=[CH:31][CH:30]=1

参加物

5

反応物 2

HCID 7815p-ChlorothiophenolHCID 86751471HCID 86751471、化合物

生成物 1

HCID 67597008HCID 67597008、化合物収率 77.7%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8076Glycol monoethyl ether溶媒

実験手順

To a solution 11-chloro-5-methylbenzofuro[3, 2-b]quinoline trifluoromethanesulfonate from Example 56 (65 mg, 0.156 mmol) in 2-ethoxyethanol (5 ml) was added 4-chlorothiophenol (23 mg, 0.156 mmol) causing the reaction mixture to became a bright yellow. After 5-7 min, TLC showed the disappearance of the starting material. The reaction mixture was cooled to room temperature, diluted with hexane (100 mL), cooled below room temperature, filtered and dried to afford 50 mg (63%) of the title compound, mp 150°-151° C.; 1H NMR (CDCl3) δ 8.71 (d, 1H, J=7.6), 8.60 (s, 2H), 8.23 (s, 1H), 7.96 (s, 1H), 7.86 (t, 1H, J=6.8), 7.64 (m, 2H), 7.44-7.37 (m, 4H), 5.06 (s, 3H); 13C NMR (CDCl3) δ 159.65, 146.54, 140.91, 139.53, 137.16, 136.95, 136.13, 135.33, 135.10, 130.24, 129.26, 127.46, 126.74, 126.65, 126,48, 126.08, 119.23, 116.29, 113.54, 41.25; MS (FAB, m/z) 376 (M+).

後処理

  1. temperaturecooled below room temperature
  2. filtrationfiltered
  3. customdried

出典と根拠

ORDレコード
ord-0a184aeb0f10460489d9ec4390f2be10
出典データセット
uspto-grants-1997_10
特許番号
US05681958

反応ノート

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