Sodium Sulfide → HCID 501227, compound

HRID 2300989Notes

Reaction equation

HRID 2300989 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:9].[S-2:10].[Na+].[Na+].[CH3:13][C:14]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:15]=1[CH2:16]Cl>O>[Cl:8][C:7]1[C:2]([S:10][CH2:16][C:15]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:14]=2[CH3:13])=[N+:3]([O-:9])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 69987Benzene, 2-(chloromethyl)-1,4-dimethyl-HCID 217853002,3-Dichloro-1-oxo-1lambda~5~-pyridine

Product 1

HCID 501227HCID 501227, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,3-Dichloropyridine N-oxide (4.3 g, 0.026 mole) (prepared according to U.S. Pat. No. 3,850,939) and sodium sulfide (3.4 g, 0.026 mole) were mixed with 25 mL of water and then heated to 70 degrees for two hours. The resulting mixture was cooled to room temperature and treated with 2,5-dimethylbenzyl chloride (4.3 g, 0.026 mole) drop wise. After the addition, the mixture was heated to 70 degrees for four hours, then cooled in an ice bath. The precipitated solid was filtered and washed with cold toluene leaving 3.5 g of product. Recrystallization from toluene afforded pure product having a melting point of 77-80° C. The compound was identified by its NMR spectrum. NMR data (CDCl3): 2.3 (s, 6H); 4.5 (s, 2H); 7.1-8.0 (m, 6H).

Workup

  1. temperatureheated to 70 degrees for two hours
  2. additionAfter the addition
  3. temperaturethe mixture was heated to 70 degrees for four hours
  4. temperaturecooled in an ice bath
  5. filtrationThe precipitated solid was filtered
  6. washwashed with cold toluene leaving 3.5 g of product
  7. customRecrystallization from toluene afforded pure product

Sources & evidence

ORD record
ord-b0058042e81049399ee0dbe6f37ccbe0
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

Loading…