Phenyl isocyanate → HCID 15906598, compound

HRID 1250485Notes

Reaction equation

HRID 1250485 reaction equation
Br[C:2]1[CH:7]=[C:6]([N:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:3]=1.CCCCCC.[Li]CCCC.[C:39]1([N:45]=[C:46]=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(OCC)C>[C:39]1([NH:45][C:46]([C:2]2[CH:7]=[C:6]([N:8]([CH3:16])[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[C:4]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:3]=2)=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8058HexaneHCID 21249824HCID 21249824, compoundHCID 178418339Butyllithium

Product 1

HCID 15906598HCID 15906598, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1.00 g (0.0023 mol) of 2-bromo-4-{methyl(phenylmethyl) amino}-6-{3-(trifluoromethyl)phenoxy} pyridine was dissolved in about 20 ml of diethyl ether. While cooling the solution in a dry ice-acetone bath in an argon atmosphere, 2.2 ml of a 1.6M-hexane solution of BuLi (0.0023×1.5 mol) was added to the solution, followed by stirring the obtained mixture for about 10 minutes. After 0.62 g (0.0023×2.3 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 one hour. 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. stirringstirred at room temperature for about one hour
  5. additionThe reaction solution was mixed with about 5 ml of a 1.2N-aqueous hydrochloric acid solution
  6. washby washing with saturated sodium bicarbonate water and saturated brine
  7. dry with materialThe organic phase of the obtained solution was dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. washsubjected to silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  10. customto separate a main fraction
  11. concentrationThe fraction was concentrated
  12. customsubjected to precipitation

Sources & evidence

ORD record
ord-f08345f5d5e34c50aed4ebfd18b52ea9
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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