Cyanuric chloride → HCID 58101013, compound

HRID 222624Notes

Reaction equation

HRID 222624 reaction equation
ClC1N=C(Cl)N=C(Cl)N=1.[CH2:10]([O:17][C:18]1[C:23](=[O:24])[N:22]2[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:21]2=[N:20][C:19]=1[CH:30]=[N:31]O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:10]([O:17][C:18]1[C:23](=[O:24])[N:22]2[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:21]2=[N:20][C:19]=1[C:30]#[N:31])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 8857Ethyl AcetateHCID 76655923HCID 76655923, compound

Product 1

HCID 58101013HCID 58101013, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Trichloro-1,3,5-triazine (576 mg, 3.15 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF) (1 mL) and stirred at room temperature for 30 min. To this solution was added dropwise a solution of the product from Example 11.1 (927 mg, 3 mmol) in DMF (5 mL). The mixture was kept at room temperature for 2 h, then ethyl acetate (50 mL) was added and the organic phase separated and washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by short flash chromatography afforded the desired compound (530 mg, 60.7%).

Workup

  1. waitThe mixture was kept at room temperature for 2 h
  2. customthe organic phase separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by short flash chromatography

Sources & evidence

ORD record
ord-58980e01b5e744c0976b07bbe61300e0
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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