Thionyl Chloride → HCID 21913155, compound

HRID 1245965Notes

Reaction equation

HRID 1245965 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-7277d534c69d4238a9a56d33c87bef29
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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