Thionyl Chloride → HCID 21913155, compound

HRID 1008073Notes

Reaction equation

HRID 1008073 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[C:11]([CH3:12])=[C:10]([NH:13][CH2:14][CH2:15][CH2:16]O)[C:9]([N+:18]([O-:20])=[O:19])=[C:8]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=1>ClCCl>[ClH:3].[Cl:3][CH2:16][CH2:15][CH2:14][NH:13][C:10]1[C:9]([N+:18]([O-:20])=[O:19])=[C:8]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=[C:6]([CH3:5])[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21913299HCID 21913299, compound

Product 1

HCID 21913155HCID 21913155, compoundYield 187%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2.86 mL, 39.2 mmol) was added to a chilled (0° C.) solution of 3-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]propan-1-ol (11.3 g, 35.6 mmol) in dichloromethane (170 mL). The reaction mixture was stirred at ambient temperature for 0.5 hr and then heated at reflux for 0.5 hr. The reaction mixture was allowed to cool to ambient temperature. A precipitate was isolated by filtration and then dried under vacuum to provide 13.64 g of N-(3-chloropropyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine hydrochloride.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.5 hr
  3. temperatureto cool to ambient temperature
  4. customA precipitate was isolated by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-307a80884b0341d5ab385a8702c85354
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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