Thionyl Chloride → HCID 67512533, compound

HRID 1801524Notes

Reaction equation

HRID 1801524 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:11]1[CH2:16][CH2:15][C:14]2[S:17][CH:18]=[CH:19][C:13]=2[CH2:12]1)[CH2:9]O.S(Cl)([Cl:22])=O>C1COCC1>[Cl:22][CH2:9][CH:8]([N:11]1[CH2:16][CH2:15][C:14]2[S:17][CH:18]=[CH:19][C:13]=2[CH2:12]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 56971604HCID 56971604, compound

Product 1

HCID 67512533HCID 67512533, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridine-5-yl)ethanol (9.7 g, 33.1 mmol) in THF (280 mL) was added thionyl chloride (7.9 g, 66.2 mmol) drop-wise. The solution was stirred at room temperature for 1.5 h (monitored by TLC). The excess thionyl chloride was evaporated under reduced pressure. The residue was dissolved in CH2Cl2 (200 mL), washed with saturated NaHCO3 solution (to pH=7), dried over Na2SO4, and concentrated under vacuum to provide 5-[2-chloro-1-(2-chlorophenyl)ethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (10.1 g, 98.1%) as a light yellow oil. 1H NMR (Field: 300 MHz, Solvent: CDCl3/TMS) δ (ppm): 7.63 (d, J=6.3 Hz, 1H), 7.36-7.22 (m, 3H), 7.05 (d, J=5.1 Hz, 1H), 6.70 (d, J=5.1 Hz, 1H), 5.62 (t, J=6.3, 1H), 3.71 (s, 2H), 3.10-3.07 (m, 2H), 2.95-2.91 (m, 2H), 2.86-2.84 (m, 2H). 13C NMR (Field: 75 MHz, Solvent: CDCl3/TMS) δ (ppm): 137.72, 133.43, 132.79, 129.56, 129.47, 129.00, 127.43, 125.31, 122.70, 64.37, 56.60, 53.24, 50.98, 25.24. MS (HR, GC-CI): Calculated for C15H15Cl2NS (MH)+: 312.0375, found 312.0349.

Workup

  1. customThe excess thionyl chloride was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (200 mL)
  3. washwashed with saturated NaHCO3 solution (to pH=7)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b25d13ccb218486799da8b7dc09a421a
Source dataset
uspto-grants-2013_01
Patent number
US08349833B2

Reaction notes

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