Potassium Carbonate → HCID 67025581, compound

HRID 2390556Notes

Reaction equation

HRID 2390556 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10]Br.[NH:12]1[CH2:17][CH2:16][S:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][N:12]1[CH2:17][CH2:16][S:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 114713444-Bromo-3-(bromomethyl)benzonitrile

Product 1

HCID 67025581HCID 67025581, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-3-(bromomethyl)benzonitrile (0.95 g, 3.46 mmol) in DMF (13.40 ml) was added thiomorpholine (0.417 ml, 4.15 mmol) and potassium carbonate (0.573 g, 4.15 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was poured onto water and extracted with EtOAc (×2). The organic extractions were combined, washed with brine (×3), dried (MgSO4) and evaporated to give a yellow oil. This was purified by flash silica chromatography (Biotage column) (eluent=25% ether/isohexane) to give the sub-title compound as a colourless oil. Yield: 0.951 g

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionextracted with EtOAc (×2)
  3. extractionThe organic extractions
  4. washwashed with brine (×3)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a yellow oil
  8. customThis was purified by flash silica chromatography (Biotage column) (eluent=25% ether/isohexane)

Sources & evidence

ORD record
ord-0646e4ae0e224ab0baa719368fd53e75
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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