Trichloroisocyanuric Acid → HCID 59949122, compound

HRID 2387765Notes

Reaction equation

HRID 2387765 reaction equation
[OH:1][C@@H:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl>[CH:12]1([CH2:11][C@H:2]([OH:1])[C:3]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)=[O:4])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 15172765HCID 15172765, compound

Product 1

HCID 59949122HCID 59949122, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2 (1.02 g, 5.39 mmol, 1 eq) is dissolved in 60 mL of dry DCM and cooled to 0° C. Trichloroisocyanuric acid (1.32 g, 5.65 mmol, 1.05 eq) is added and mixed for 10 minutes resulting in a white slurry. TEMPO is added (8.8 mg, 0.056 mmol, 0.01 eq) to the chilled reaction mixture which immediately turns orange and additional precipitate is formed. The reaction vessel is removed from the cold bath and the mixture is stirred for additional 45 minutes. The reaction mixture is then filtered through a pad of celite, washed with 5% citric acid followed by saturated bicarbonate, dried over MgSO4, filtered, and stripped to yield pure 3 (0.979 g, 97% yield) which was used immediately in step C.

Workup

  1. additionmixed for 10 minutes
  2. customresulting in a white slurry
  3. customto the chilled reaction mixture which immediately turns orange
  4. customadditional precipitate is formed
  5. customThe reaction vessel is removed from the cold bath
  6. filtrationThe reaction mixture is then filtered through a pad of celite
  7. washwashed with 5% citric acid
  8. dry with materialdried over MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c89bd2ccd68443ad8ebdc957cc52188c
Source dataset
uspto-grants-2012_09
Patent number
US08268996B2

Reaction notes

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