p-Chlorothiophenol → HCID 67597008, 화합물

HRID 582672노트

반응식

HRID 582672 반응식
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

참가 물질

5

반응물 2

HCID 7815p-ChlorothiophenolHCID 86751471HCID 86751471, 화합물

생성물 1

HCID 67597008HCID 67597008, 화합물수율 77.7%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8076Glycol monoethyl ether용매

실험 절차

To a solution 11-chloro-5-methylbenzofuro[3,2b]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) δ8.71 (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, 25 135.10, 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+).

후처리

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

출처 및 근거

ORD 기록
ord-2ac1e5ee89d44f429bfab4006949a1c2
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925647

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