Cyanuric chloride → HCID 59216379, compound

HRID 2069808Notes

Reaction equation

HRID 2069808 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][C:19]([NH2:21])=O)[CH:14]=3)[C:9]2=[O:22])=[CH:5][CH:4]=1.N1C(Cl)=NC(Cl)=NC=1Cl>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][C:19]#[N:21])[CH:14]=3)[C:9]2=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 59216414HCID 59216414, compound

Product 1

HCID 59216379HCID 59216379, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.3 g of 2-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-acetamide in 5 mL of THF and 10 mL of DMF was added 370 mg of cyanuric chloride and after stirring at room temperature for 0.5 hour, the reaction mixture was partitioned between ethyl acetate and brine. The organic layer was washed with 5% sodium bicarbonate, followed by brine and then dried over sodium sulfate. Purification by flash chromatograpy on silica gel column using 75% ethyl acetate in hexane as eluent afforded 1.2 g of [2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-acetonitrile.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and brine
  2. washThe organic layer was washed with 5% sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customPurification by flash chromatograpy on silica gel column

Sources & evidence

ORD record
ord-37f7bdda31af4becb6266168e5a16ccc
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…