p-Chlorothiophenol → HCID 67597008, compound

HRID 1490306Notes

Reaction equation

HRID 1490306 reaction equation
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

Participants

5

Reactant 2

HCID 7815p-ChlorothiophenolHCID 86751471HCID 86751471, compound

Product 1

HCID 67597008HCID 67597008, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-0a184aeb0f10460489d9ec4390f2be10
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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