Ethanethiol → HCID 22907024, compound

HRID 1379699Notes

Reaction equation

HRID 1379699 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(S)C.[CH3:8][N:9]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:25]([C:26]3[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=3)=[CH:24][CH:23]=[C:22]([CH3:34])[N:21]=2)=[CH:16][CH:15]=1)[CH3:10]>ClCCCl>[CH3:10][N:9]([CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:25]([C:26]3[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=3)=[CH:24][CH:23]=[C:22]([CH3:34])[N:21]=2)=[CH:18][CH:19]=1)[CH3:8]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18923784HCID 18923784, compound

Product 1

HCID 22907024HCID 22907024, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

The AlCl3 (7 g, 52 mmol) was stirred in 150 mL of DCE at 0° C., ethanethiol (5.5 mL, 75 mmol) was added, and the mixture stirred for 15 min. The 2-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-methylpyridine (2.7 g, 7.5 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 25 mL THF at 0° C., followed by 25 mL 1N HCl and worked up. The crude product was recrystallised from hot EtOAc/ pet. ether to give 0.9 g (34 % yield) of white solid: mp 155°-157° C.; 1H NMR (CDCl3) d 2.37 (s, 6H, NCH3), 2.62 (s, 3H, pyr-CH3), 2.78-2.81 (t, 2H, J=5 Hz, CH2N), 4.05-4.07 (t, 2H, J=5 Hz, OCH2), 6.64-6.69 (m, 4H, ArH), 6.94-6.96 (d, 2H, J=8 Hz, ArH), 7.09-7.12 (d, 1H, J=8 Hz, ArH), 7.24-7.27 (comp, 2H, ArH), 7.52-7.55 (d, 1H, J=8 Hz, ArH); MS(FD) 348 (M+). Anal. Calcd for C22H24 N2O2 : C, 75.84; H, 6.94; N, 8.04. Found: C, 75.70; H, 6.98; N, 8.00.

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 recrystallised from hot EtOAc/ pet. ether

Sources & evidence

ORD record
ord-3f352e0a5d04469ea7abef9ca0c7d936
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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