Thionyl Chloride → HCID 21913840, compound

HRID 1008069Notes

Reaction equation

HRID 1008069 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]O)[C:9]([N+:19]([O-:21])=[O:20])=[C:8]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:7]=1>ClCCl>[Cl:3][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:10]1[C:9]([N+:19]([O-:21])=[O:20])=[C:8]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:7]=[C:6]([CH3:5])[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21914017HCID 21914017, compound

Product 1

HCID 21913840HCID 21913840, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (3.14 mL, 43 mmol) was added over a period of 5 minutes to a chilled (0° C.) solution of 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butan-1-ol (12.95 g, 39.08 mmol) in dichloromethane (130 mL). The reaction was allowed to warm to ambient temperature and was stirred overnight under a nitrogen atmosphere. The reaction mixture was diluted with dichloromethane (130 mL), washed sequentially with saturated aqueous sodium bicarbonate (2×65 mL), water (80 mL) and brine (100 mL), dried over magnesium sulfate, filtered and then concentrated under reduced pressure to provide 12.57 g of N-(4-chlorobutyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine as a yellow solid.

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate (2×65 mL), water (80 mL) and brine (100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb595a4198dd44ab80563d72c964a467
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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