Thionyl Chloride → HCID 21913056, compound

HRID 1245909Notes

Reaction equation

HRID 1245909 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][CH2:17][CH2:18]O)[C:9]([N+:20]([O-:22])=[O:21])=[C:8]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:7]=1>ClCCl>[Cl:3][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:10]1[C:9]([N+:20]([O-:22])=[O:21])=[C:8]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:7]=[C:6]([CH3:5])[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21913716HCID 21913716, compound

Product 1

HCID 21913056HCID 21913056, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (10.72 mL, 147 mmol) was added dropwise to a mixture of 5-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]pentan-1-ol (34.0 g, 98 mmol) and dichloromethane (250 mL). The reaction mixture was heated at reflux for 2 hours and then it was placed in an ice bath and quenched with water. The reaction mixture was concentrated under reduced pressure. The residue was combined with water (300 mL). Solid sodium bicarbonate was slowly added to pH 10; then the mixture was extracted with ethyl acetate (250 mL). The extract was washed sequentially with saturated sodium bicarbonate (2×100 mL) and brine (1×100 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 30.96 g of N-(5-chloropentyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customit was placed in an ice bath
  4. customquenched with water
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionSolid sodium bicarbonate was slowly added to pH 10
  7. extractionthen the mixture was extracted with ethyl acetate (250 mL)
  8. washThe extract was washed sequentially with saturated sodium bicarbonate (2×100 mL) and brine (1×100 mL)
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45a8e97040f9405f87ae28ad3e4bce4c
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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