Ethanethiol → HCID 22907019, compound

HRID 1379702Notes

Reaction equation

HRID 1379702 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]([CH3:37])[N:24]=3)=[CH:19][CH:18]=2)[CH2:13][CH2:12][O: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:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=4)=[CH:27][CH:26]=[C:25]([CH3:37])[N:24]=3)=[CH:21][CH:22]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18923791HCID 18923791, compound

Product 1

HCID 22907019HCID 22907019, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

The AlCl3 (5 g, 38 mmol) was stirred in 100 mL of DCE at 0° C., ethanethiol (4 mL, 54 mmol) was added, and the mixture stirred for 15 min. The 2-[4-[2-(4-morpholinyl)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-methylpyridine (2.2 g, 5.4 mmol) in 50 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 50 mL THF at 0° C., followed by 50 mL 1N HCl and worked up. The crude product was triturated with Et2O/ pet. ether, filtered, and dried in vacuo to give 1.9 g (90 % yield) of white solid: mp 75-80 ° C.; 1H NMR (CDCl3) d 2.59-2.62 (comp, 7H, morpholine and pyr-CH3), 2.79-2.83 (t, 2H, J=5 Hz, CH2N), 3.74-3.77 (m, 4H, morpholine), 4.07-4.11 (t, 2H, J=5 Hz, OCH2), 6.63-6.71 (m, 4H, ArH), 6.94-6.97 (d, 2H, J=8 Hz, ArH), 7.11-7.13 (d, 1H, J=8 Hz, ArH), 7.24-7.27 (d, 2H, J=8 Hz, ArH), 7.53-7.56 (d, 1H, J=8 Hz, ArH); MS(FD) 390 (M+). Anal. Calcd for C24H26N3O3 : C, 73.82; H, 6.71; N, 7.17. Found: C, 73.75; H, 6.71; N, 7.05.

Workup

  1. stirringstirred for 2 h as it
  2. customto come to rt
  3. customquenched with 50 mL THF at 0° C.
  4. customThe crude product was triturated with Et2O/ pet. ether
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-aee0e01f803a4b57acddf0150d9a4b9d
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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