Trichloroisocyanuric Acid → HCID 22049781, compound

HRID 1830899Notes

Reaction equation

HRID 1830899 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[S:11][CH:12]=1.[Cl:24]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>CN(C=O)C.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[Cl:24][C:12]1[S:11][C:10]([C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[N:9][C:8]=1[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 22049695HCID 22049695, compound

Product 1

HCID 22049781HCID 22049781, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 86584982Sodium bicarbonate ethyl acetateSolvent

Procedure

To a solution of 3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]-N,N-dimethylbenzamide (400 mg) in DMF (2 ml) was added trichloroisocyanuric acid (120 mg) and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with aqueous sodium hydrogen carbonate-ethyl acetate. The organic layer was separated and washed with water, aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried and concentrated, and the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification to give the title compound (140 mg) as a colorless amorphous compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, aqueous sodium hydrogen carbonate and saturated brine
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification

Sources & evidence

ORD record
ord-0d36d00b0b8d46f3a902c0563cd9d65f
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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