1-Bromooctane → HCID 118274780, compound

HRID 628926Notes

Reaction equation

HRID 628926 reaction equation
[C:1]([C:3]1[C:11]([C:12]#[N:13])=[CH:10][C:6]2[NH:7][N:8]=[N:9][C:5]=2[CH:4]=1)#[N:2].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].CC(C)([O-])C.[K+]>CO>[CH2:15]([N:8]1[N:7]=[C:6]2[CH:10]=[C:11]([C:12]#[N:13])[C:3]([C:1]#[N:2])=[CH:4][C:5]2=[N:9]1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 23665647Potassium tert-butoxideHCID 178509432HCID 178509432, compound

Product 1

HCID 118274780HCID 118274780, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,6-Dicyano-1H-benzotriazole (169 mg, 1.0 mmol), 1-bromooctane (195 mg, 1.0 mmol), potassium tert-butoxide (113 mg, 1 mmol), and methanol (5 mL) were mixed in a round-bottomed flask equipped with a condenser. The reaction mixture was refluxed overnight. The mixture was cooled down to room temperature and methanol was removed with a rotary evaporator. The resulting mixture was then extracted with CHCl3 and the organic phase was washed with water and dried over Na2SO4. The resulting off-white solid was purified by column chromatography (80 mg, 30%).

Workup

  1. customequipped with a condenser
  2. temperatureThe reaction mixture was refluxed overnight
  3. custommethanol was removed with a rotary evaporator
  4. extractionThe resulting mixture was then extracted with CHCl3
  5. washthe organic phase was washed with water
  6. dry with materialdried over Na2SO4
  7. customThe resulting off-white solid was purified by column chromatography (80 mg, 30%)

Sources & evidence

ORD record
ord-6726cecac020497590a9bee972468323
Source dataset
uspto-grants-2016_04
Patent number
US09315477B2

Reaction notes

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