Dimethylformamide → HCID 15906595, compound

HRID 1250482Notes

Reaction equation

HRID 1250482 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Br[C:15]1[CH:20]=[C:19]([S:21][CH3:22])[CH:18]=[C:17](Br)[N:16]=1.[CH3:24][N:25]([CH:27]=[O:28])C>CCCCCC>[C:24]1([NH:25][C:27]([C:15]2[CH:20]=[C:19]([S:21][CH3:22])[CH:18]=[C:17]([O:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=3)[N:16]=2)=[O:28])[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 54276775HCID 54276775, compound

Product 1

HCID 15906595HCID 15906595, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

2.06 g (0.0106×1.2 mol) of 3-(trifluoromethyl) phenol was dissolved in about 20 ml of DMF. The solution was further mixed with 0.45 g (ca. 60% in mineral oil; 0.0106×1.06 mol) of NaH and then with 3.00 g (0.0106 mol) of 2,6-dibromo-4-methylmercapto pyridine. After stirring at about 110° C. for about 2 hours, the mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed in hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), and the obtained eluate was subjected to recrystallization using hexane, thereby obtaining an aimed product.

Workup

  1. temperaturefor cooling to room temperature
  2. washthe organic phase of the obtained solution was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe resultant solution was concentrated
  5. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  6. customthe obtained eluate was subjected to recrystallization

Sources & evidence

ORD record
ord-fe460f794bfe4fe88382f1046a7fa93f
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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