Water → HCID 66913662, compound

HRID 2104611Notes

Reaction equation

HRID 2104611 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[N:10][C:11]3[C:16]([C:17]=2O)=[CH:15][CH:14]=[CH:13][C:12]=3[C:19]([F:22])([F:21])[F:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=N[C:27]2[C:32](C=1O)=[CH:31][CH:30]=[CH:29][C:28]=2C(F)(F)F.C1(S)C=CC=CC=1.[Na].O>CN(C=O)C>[C:27]1([C:17]2[C:16]3[C:11](=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 66586497Sodium benzenethiolHCID 178515289HCID 178515289, compoundHCID 178516911HCID 178516911, compound

Product 1

HCID 66913662HCID 66913662, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-(phenylthio)-8-(trifluoromethyl)quinolin-4-ol: A solution of 3-bromo-8-(trifluoromethyl)quinolin-4-ol (0.240 g, 0.830 mmol), sodium thiophenol (0.293 g, 45.1 mmol), is dissolved in DMF and heated in a microwave reactor for 10 min at 120° C. After which, the reaction is poured into water and extracted with ethyl acetate. The combined extracts are washed with sat aq NaHCO3, water, brine, and dried with magnesium sulfate. The extracts are concentrated and the residue is chromatographed with 1:9 ethyl acetate:hexanes to afford the title compound as a white solid (0.151 g, 57%). mp 153-155° C.; MS (ESI) m/z 322; MS (ESI) m/z 320; HRMS: calcd for C16H10NF3OS+H, 322.05134; found (ESI, [M+H]+), 322.0486.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts are washed with sat aq NaHCO3, water, brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe extracts are concentrated
  5. customthe residue is chromatographed with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-cb8b9bb1afaf4672b8e9d8e9dfa9e1f7
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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