Diethyl Ether → HCID 21696655, compound

HRID 378798Notes

Reaction equation

HRID 378798 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[N:6]=1)=[O:4].S(Cl)([Cl:19])(=O)=O.CCOCC>CC#N>[NH2:11][C:9]1[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[N:6]=[C:5]([C:3]([OH:2])=[O:4])[C:10]=1[Cl:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24648Sulfuryl chlorideHCID 21696665HCID 21696665, compound

Product 1

HCID 21696655HCID 21696655, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution containing 4-amino-6-trifluoromethylpyridine-2-carboxylic acid methyl ester (0.75 g, 3.4 mmol) in 5 mL of CH3CN was added dropwise a solution of sulfuryl chloride (0.27 mL, 3.4 mmol) in 1 mL of CH3CN. After stirring at RT for 1 hr, reaction mixture was added to 50 mL of Et2O and washed with aqueous NaHCO3, dried over MgSO4, filtered and concentrated to give a solid. The crude product was purified by chromatography, eluting with 10% ethyl acetate-hexane to give 200 mg of product as a white solid; mp 131-3° C.

Workup

  1. customreaction mixture
  2. washwashed with aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid
  7. customThe crude product was purified by chromatography
  8. washeluting with 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-c978264ac98144848208ae70e0947b21
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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