Cyanuric chloride → HCID 23135159, compound

HRID 475517Notes

Reaction equation

HRID 475517 reaction equation
[O:1]=[C:2]1[CH2:22][C:5]2[C:6]([C:19]([NH2:21])=O)=[N:7][N:8]([S:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)(=[O:11])=[O:10])[C:4]=2[CH2:3]1.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[O:1]=[C:2]1[CH2:22][C:5]2[C:6]([C:19]#[N:21])=[N:7][N:8]([S:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)(=[O:11])=[O:10])[C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 58713626HCID 58713626, compound

Product 1

HCID 23135159HCID 23135159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the intermediate from step E above (0.91 mmol) in anhydrous DMF (5 mL) was added cyanuric chloride (334 mg, 2.0 mmol) in two portions. After stirring at room temperature for 15 minutes, the reaction was quenched by pouring into water (10 mL). The resulting mixture was extracted with ethyl acetate, washed with saturated NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2) using 25% ethyl acetate-hexaries. A white solid was obtained.

Workup

  1. customthe reaction was quenched
  2. additionby pouring into water (10 mL)
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washwashed with saturated NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (SiO2)
  9. customA white solid was obtained

Sources & evidence

ORD record
ord-f7d9d95a54484a388c76e41abb86cf62
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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