Trichloroisocyanuric Acid → HCID 18963857, compound

HRID 2226977Notes

Reaction equation

HRID 2226977 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[S:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:10]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)Cl.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>[Cl:10][C:7]1[C:5]2[N:6]=[C:2]([CH3:1])[S:3][C:4]=2[S:9][CH:8]=1

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 12455099HCID 12455099, compound

Product 1

HCID 18963857HCID 18963857, compoundYield 218.1%

Reagents, catalysts & solvents 2

HCID 6909Trichloroisocyanuric AcidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.18 g (7.2 mmol) of 2-methylthieno[3.2-d]thiazole (from Step 1) in 35 ml of CH2Cl2 was added 670 mg (2.9 mmol) of trichloroisocyanuric acid at 0° C. The reaction was stirred at 0° C. for 30 min., then at r.t. for 2 h.; 60 mg (0.26 mmol) of trichloroisocyanuric acid was again added, and the reaction was stirred at r.t. for another hour. The product was partitioned between CH2Cl2 and aqueous NaHCO3. Chromatographic purification on silica gel using hexane/EtOAc=5:1 afforded 1.2 g (90%) of the title product. 1H NMR (CDCl3) 7.28(s, 1H), 2.82(s, 3H).

Workup

  1. waitat r.t. for 2 h.
  2. stirringthe reaction was stirred at r.t. for another hour
  3. customThe product was partitioned between CH2Cl2 and aqueous NaHCO3
  4. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-4c2f685c86434a0db6e41fceb389fdc2
Source dataset
uspto-grants-1994_09
Patent number
US05350760

Reaction notes

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