Cyanuric chloride → HCID 23135168, compound

HRID 475507Notes

Reaction equation

HRID 475507 reaction equation
[CH2:1]([N:8]1[C:12]2[CH2:13][C:14](=[O:16])[CH2:15][C:11]=2[C:10]([C:17]([NH2:19])=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[CH2:1]([N:8]1[C:12]2[CH2:13][C:14](=[O:16])[CH2:15][C:11]=2[C:10]([C:17]#[N:19])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 58713637HCID 58713637, compound

Product 1

HCID 23135168HCID 23135168, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the intermediate from step E (5.25 mmol) in DMF (60 mL) was added cyanuric chloride (3.12 g, 17 mmol) in three portions. After 30 minutes at room temperature, the reaction was quenched with water and extracted with ethyl acetate (2×). The organic layer was washed with water, brine and dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2) using 30% ethyl acetate-hexanes to give the desired product (0.95 g) as a yellow solid.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with ethyl acetate (2×)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-8aeaa62b7ed34ef3a4ea97143e4939f0
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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