4-Toluenesulfonyl chloride → HCID 18511471, compound

HRID 1370343Notes

Reaction equation

HRID 1370343 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:12]=[C:11]([CH:13]([OH:18])[CH2:14][CH2:15][CH2:16]O)[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:21])[F:20])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:23][C:2]([F:24])([F:1])[C:3]1[CH:12]=[C:11]([CH:13]2[CH2:14][CH2:15][CH2:16][O:18]2)[C:10]2[C:5](=[C:6]([C:19]([F:20])([F:21])[F:22])[CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 18511424HCID 18511424, compound

Product 1

HCID 18511471HCID 18511471, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2,8-bis(trifluoromethyl)-4-quinolinyl)-4-hydroxybutanol (176 mg, 0.5 mmol) in CH2Cl2 (5 mL) was treated with p-toluenesulphonyl chloride (102 mg, 0.55 mmol) and triethylamine (0.084 mL, 0.6 mmol) and stirred at room temperature for 16 h. The mixture was poured into saturated NaHCO3 solution (10 mL), extracted with CH2Cl2 (2×10 mL) and the combined organic phase dried (MgSO4), concentrated in vacuo, purified by chromatography [SiO2, heptane-EtOAc (95:5)] and the resulting solid triturated with cold hexane and filtered to give the title compound (111 mg, 66%) as a white solid: mp 61.0-61.7° C.; IR νmax (Nujol)/cm−1 3096, 2924, 2854, 1603, 1585, 1516, 1463, 1431, 1308, 1178, 1100, 1086 and 775; NMR δH (400 MHz, CDCl3) 1.79-1.86 (1H, m), 2.00-2.16 (2H, m), 2.63-2.71 (1H, m), 4.08 (1H, q, J 7.3 Hz), 4.24-4.29 (1H, m), 5.63 (1H, t, J 7.3 Hz), 7.72 (1H, t, J 7.7 Hz), 7.99 (1H, s), and 8.14-8.18 (2H, m).

Workup

  1. extractionextracted with CH2Cl2 (2×10 mL)
  2. dry with materialthe combined organic phase dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography [SiO2, heptane-EtOAc (95:5)]
  5. customthe resulting solid triturated with cold hexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6a671e502a35466baaa7343e02e608b8
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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