Sodium Sulfide → HCID 501227, compound

HRID 1829732Notes

Reaction equation

HRID 1829732 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

Conditions

Temperature
70 °C

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 then heated to 70° C. 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° C. 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 of m.p. 77–80° C. The compound was identified by its NMR spectrum.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. additionAfter the addition
  3. temperaturethe mixture was heated to 70° C. 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 of m.p. 77–80° C

Sources & evidence

ORD record
ord-283e317c71304008a86cce2dd12b3305
Source dataset
uspto-grants-2006_06
Patent number
US07064139B2

Reaction notes

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