Ethanethiol → HCID 11003284, compound

HRID 1379700Notes

Reaction equation

HRID 1379700 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(S)C.[N:8]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:27]([C:28]4[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=4)=[CH:26][CH:25]=[C:24]([CH3:36])[N:23]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1>ClCCCl>[N:8]1([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:27]([C:28]4[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=4)=[CH:26][CH:25]=[C:24]([CH3:36])[N:23]=3)=[CH:20][CH:21]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 11731847HCID 11731847, compound

Product 1

HCID 11003284HCID 11003284, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

The AlCl3 (3.6 g, 27 mmol) was stirred in 100 mL of DCE at 0° C., ethanethiol (3 mL, 38 retool) was added, and the mixture stirred for 15 min. The 2-[4-[2-(1-pyrrolidinyl) ethoxy]phenyl]-3- (4-methoxyphenyl) -6-methylpyridine (1.5 g, 3.9 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 75 mL THF at 0° C., followed by 50 mL 1N HCl and worked up. The crude product was triturated with Et2O, filtered, and dried in vacuo to give 1.3 g (90 % yield) of an off-white solid: mp 159°-161° C.; 1H NMR (CDCl3) d 1.80-184 (bs, 4H, pyrrolidine), 2.61 (s, 3H, pyr-CH3), 2.67-2.69 (bs, 4H, pyrrolidine), 2.93-2.97(m, 2H, CH2N), 4.08-4.10 (m, 2H, OCH2), 6.60-6.65 (m, 4H, ArH), 6.90-6.93 (d, 2H, J=8 Hz, ArH), 7.08-7.11 (d, 1H, J=8 Hz, ArH), 7.23-7.26 (m, 2H, ArH), 7.50-7.53 (d, 1H, J=8 Hz, ArH); MS(FD) 374(M+). Anal. Calcd for C24H26N2O2 : C, 76.98; H, 7.00; N, 7.48. Found: C, 76.70; H, 7.07; N, 7.36.

Workup

  1. stirringstirred for 2 h as it
  2. customto come to rt
  3. customquenched with 75 mL THF at 0° C.
  4. customThe crude product was triturated with Et2O
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-92c09a8b4eda49448f8cd4752c6fb02f
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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