Potassium Carbonate → HCID 66678677, compound

HRID 2410550Notes

Reaction equation

HRID 2410550 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.BrN1C(=O)CCC1=O.Cl.[C:20]([O:24][C:25](=[O:29])[CH2:26][NH:27][CH3:28])([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O.CC(N=NC(C#N)(C)C)(C#N)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH2:1][N:27]([CH3:28])[CH2:26][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:29])=[CH:3][C:4]=1[Cl:10])#[N:7]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 3194752-Chloro-4-methylbenzonitrileHCID 11252350Sarcosine t-butyl ester hydrochloride

Product 1

HCID 66678677HCID 66678677, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-methyl-2-chlorobenzonitrile (1.51 g, 10 mmol), N-bromosuccinimide (2.14 g, 12.0 mmol) and AIBN (33 mg, 0.20 mmol) in ACN (40 mL) was heated under reflux for 18 hours. The reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of Na2CO3 and brine. The organic layer was dried (MgSO4) and concentrated under vacuum. The residue was treated with sarcosine tert-butyl ester hydrochloride (1.44 g, 7.92 mmol) and K2CO3 (2.74 g, 19.8 mmol) in ACN (10 mL). The mixture was heated at 100° C. for 2 hours. The solvent was evaporated under vacuum. The residue was dissolved in a mixture of DCM and water and then poured through a hydrophobic frit. The solvent was evaporated under vacuum. The residue was purified by flash chromatography (silica, iso-hexane/Et2O) to afford the title compound (1.95 g, quantitative). 1H NMR (CDCl3, 400 MHz) δ 7.61 (1H, d, J=8.0 Hz), 7.57 (1H, s), 7.36 (1H, m), 3.73 (2H, s), 3.21 (2H, s), 2.36 (3H, s), 1.48 (9H, s).

Workup

  1. temperatureunder reflux for 18 hours
  2. washwashed with a saturated aqueous solution of Na2CO3 and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. customThe solvent was evaporated under vacuum
  6. dissolutionThe residue was dissolved in a mixture of DCM and water
  7. additionpoured through a hydrophobic frit
  8. customThe solvent was evaporated under vacuum
  9. customThe residue was purified by flash chromatography (silica, iso-hexane/Et2O)

Sources & evidence

ORD record
ord-5c9c2c803c3343e19431711e690ef4df
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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