Thiophenol → HCID 67156409, compound

HRID 549261Notes

Reaction equation

HRID 549261 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2.[OH-].[K+].[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.S(=O)(=O)(O)O>[C:18]1([S:24][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 113736-AminoquinolineHCID 14797Potassium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 67156409HCID 67156409, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A solution of sodium nitrite (1 g, 14 mmol) in water (6 mL) was slowly added to a stirred solution of 6-amino-quinoline (1.44 g, 10 mmol) in sulfuric acid (50%) (8 mL). The temperature was kept below 5° C. during the addition. The reaction mixture was poured into a solution of potassium hydroxide (9 g, 16 mmol) and thiophenol (1 mL, 9 mmol) in water (30 mL). The reaction mixture was refluxed for 3 h, cooled and extracted with diethyl ether. The insoluble material was eliminated by filtration. During filtration most of the material was trapped in the solid phase. The filtrate was evaporated and the residue was purified by column chromatography (SiO2, ethyl acetate:hexane, 1:2) to yield a colorless oil (100 mg, 4% PS: the low yield is due to the loss of the material during the filtration procedure). MS m/z: 238 [M+H+]. 1H NMR (270 MHz, CD3Cl) δ ppm 7.34 (m, 4H) 7.42 (m, 2H) 7.57 (dd, J=8.97, 2.11 Hz, 1H) 7.67 (d, J=2.11 Hz, 1H) 7.99 (m, 2H) 8.84 (dd, J=4.22, 1.58 Hz, 1H).

Workup

  1. additionThe temperature was kept below 5° C. during the addition
  2. temperatureThe reaction mixture was refluxed for 3 h
  3. temperaturecooled
  4. extractionextracted with diethyl ether
  5. filtrationThe insoluble material was eliminated by filtration
  6. filtrationDuring filtration most of the material
  7. customThe filtrate was evaporated
  8. customthe residue was purified by column chromatography (SiO2, ethyl acetate:hexane, 1:2)
  9. customto yield a colorless oil (100 mg, 4% PS
  10. customthe low yield
  11. filtrationis due to the loss of the material during the filtration procedure)

Sources & evidence

ORD record
ord-572e16f529a044c187b77461cb6e022d
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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