Ethanethiol → HCID 22907018, compound

HRID 1379703Notes

Reaction equation

HRID 1379703 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(S)C.[N:8]1([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:28]([C:29]4[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=4)=[CH:27][CH:26]=[C:25]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[N:24]=3)=[CH:19][CH:18]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>ClCCCl>[N:8]1([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:28]([C:29]4[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=4)=[CH:27][CH:26]=[C:25]([C:37]4[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=4)[N:24]=3)=[CH:21][CH:22]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18923788HCID 18923788, compound

Product 1

HCID 22907018HCID 22907018, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

The AlCl3 (1.9 g, 14 mmol) was stirred in 50 mL of DCE at 0° C., ethanethiol (1.5 mL, 20 mmol) was added, and the mixture stirred for 15 min. The 2-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-(4-fluorophenyl)pyridine (1 g, 2 mmol) in 25 mL DCE was added dropwise to the reaction mixture and stirred for 2 h as it was allowed to come to rt, then quenched with 25 mL THF at 0° C., followed by 25 mL 1N HCl and worked up. The crude product was triturated with Et2O, filtered, and dried in vacuo to give 0.86 g (91% yield) of white solid: mp 194°-195° C.; 1H NMR (CDCl3) d 1.63-167 (comp, 6H, piperidine), 2.59 (bs, 4H, piperidine), 2.81-2.84 (t, 2H, J=5 Hz, CH2N), 4.12-4.15 (t, 2H, J=5 Hz, OCH2), 6.64-6.70 (m, 4H, ArH), 7.00-7.03 (d, 2H, J=8 Hz, ArH), 7.12-7.18 (m, 2H, ArH), 7.37-7.40 (d, 2H, J=8 Hz, ArH), 7.61-7.67 (m, 2H, ArH), 8.08-8.12 (m, 2H, ArH); MS (FD) 468 (M+). Anal. Calcd for C30H29N2O2F: C, 76.90; H, 6.24; N, 5.98. Found: C, 77.13; H, 6.36; N, 5.86.

Workup

  1. stirringstirred for 2 h as it
  2. customto come to rt
  3. customquenched with 25 mL THF at 0° C.
  4. customThe crude product was triturated with Et2O
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-489f9d1155184d0ab6cdaa84705f4e48
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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