Phenyl isocyanate → HCID 15906595, compound

HRID 1250483Notes

Reaction equation

HRID 1250483 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:3]=1.CCCCCC.[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)C>[C:27]1([NH:33][C:34]([C:2]2[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)[N:3]=2)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8058HexaneHCID 177838442-Bromo-4-(methylsulfanyl)-6-[3-(trifluoromethyl)phenoxy]pyridine

Product 1

HCID 15906595HCID 15906595, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.8 g (0.0022 mol) of 2-bromo-4-methylmercapto-6-{3-(trifluoromethyl)phenoxy} pyridine was dissolved in about 15 ml of diethyl ether. While cooling the obtained solution in a dry ice-acetone bath in an argon atmosphere, 1.5 ml of a 1.6M-hexane solution of BuLl (0.0022×1.1 mol) was added to the solution, followed by stirring the resultant mixture for about 10 minutes. After 0.52 g (0.0022×2.0 mol) of phenyl isocyanate dissolved in about 5 ml of diethyl ether was added to the reaction solution, the obtained solution was removed from the bath and stirred at room temperature for about 30 minutes. The reaction solution was mixed with about 5 ml of a 1.2N-aqueous hydrochloric acid solution, and then distributed in ethyl acetate-water, followed by washing with saturated sodium bicarbonate water and saturated brine. The organic phase of the obtained solution was dried with anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluting solution: ethyl acetate/hexane) to separate a main fraction therefrom. The fraction was concentrated and then subjected to precipitation using hexane, thereby obtaining an aimed product.

Workup

  1. additionwas added to the solution
  2. additionwas added to the reaction solution
  3. customthe obtained solution was removed from the bath
  4. additionThe reaction solution was mixed with about 5 ml of a 1.2N-aqueous hydrochloric acid solution
  5. washby washing with saturated sodium bicarbonate water and saturated brine
  6. dry with materialThe organic phase of the obtained solution was dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. washsubjected to silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  9. customto separate a main fraction
  10. concentrationThe fraction was concentrated
  11. customsubjected to precipitation

Sources & evidence

ORD record
ord-e1ff742eacf64ac6b001140bc5afa1be
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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