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Dimethylformamide → HCID 15906598, compound

HRID 1250484
Notes
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Reaction equation

HRID 1250484 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+].[CH3:14][N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]1[CH:21]=[C:20](Br)[N:19]=[C:18](Br)[CH:17]=1.[CH3:31][N:32]([CH:34]=[O:35])C>CCCCCC>[C:31]1([NH:32][C:34]([C:20]2[CH:21]=[C:16]([N:15]([CH3:14])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:17]=[C:18]([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:19]=2)=[O:35])[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 183262194-{Methyl(phenylmethyl)amino}-2,6-dibromo pyridine

Product 1

HCID 15906598HCID 15906598, compound

Reagents, catalysts & solvents 1

HCID 8058
Hexane
Solvent

Procedure

1.56 g (0.0080×1.2 mol) of 3-(trifluoromethyl) phenol was dissolved in about 20 ml of DMF. The solution was further mixed with 0.34 g (ca. 60% in mineral oil; 0.0080×1.06 mol) of NaH and then with 2.85 g (0.0080 mol) of 4-{methyl(phenylmethyl)amino}-2,6-dibromo pyridine. After treating the solution under reflux for about 6 hours, the obtained reaction solution 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. additionAfter treating the solution
  2. temperatureunder reflux for about 6 hours
  3. customthe obtained reaction solution
  4. washthe organic phase of the obtained solution was washed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationThe resultant solution was concentrated
  7. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  8. customthe obtained eluate was subjected to recrystallization

Sources & evidence

ORD record
ord-3fd6a957f7f24f0c847110546722eca7
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06339045B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes