Triethylamine → HCID 67398270, compound

HRID 70720Notes

Reaction equation

HRID 70720 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH3:26])[N:19]=2)O)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C1CCCCC1>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([Cl:4])[C:18]2[N:19]=[C:20]([O:25][CH3:26])[C:21]([Cl:24])=[CH:22][CH:23]=2)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 67396476(4-Tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methanol

Product 1

HCID 67398270HCID 67398270, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Sulfuryl chloride (0.37 mL) was added to a solution of (4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methanol obtained in Example 7-4(1) (200 mg) and triethylamine (0.27 mL) in cyclohexane (4 mL) at room temperature, and then the mixture was stirred at the same temperature for 17 hours. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 6-[(4-tert-butylphenyl)(chloro)methyl]-3-chloro-2-methoxypyridine as a colorless oil (203 mg, 96%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-0c602aa7de284ba0b7a9193426a57181
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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