Potassium Carbonate → HCID 66937318, compound

HRID 919359Notes

Reaction equation

HRID 919359 reaction equation
ClC1NC2C=C(Cl)C(Cl)=CC=2N=1.C([O-])([O-])=O.[K+].[K+].CN(C)S(Cl)(=O)=O.[CH3:26][N:27]([CH3:43])[S:28]([N:31]1[C:35]2[CH:36]=[C:37]([Cl:41])[C:38]([Cl:40])=[CH:39][C:34]=2[N:33]=[C:32]1Cl)(=[O:30])=[O:29].[CH2:44]([O:46][C:47]([C:49]1[CH:50]=[N:51][NH:52][CH:53]=1)=[O:48])[CH3:45]>CN(C=O)C.O>[CH2:44]([O:46][C:47]([C:49]1[CH:50]=[N:51][N:52]([C:32]2[N:31]([S:28](=[O:30])(=[O:29])[N:27]([CH3:43])[CH3:26])[C:35]3[CH:36]=[C:37]([Cl:41])[C:38]([Cl:40])=[CH:39][C:34]=3[N:33]=2)[CH:53]=1)=[O:48])[CH3:45]

Participants

8

Reactant 5

HCID 11430Potassium Carbonate2×HCID 83372Dimethylsulphamoyl chlorideHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 2860092,5,6-Trichloro-1H-benzimidazoleHCID 66937410HCID 66937410, compound2×

Product 1

HCID 66937318HCID 66937318, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,5,6-Trichloro-1H-benzoimidazole 2 (27.6 g, 0.125 mol) was dissolved in dry DMF (200 mL) and then K2CO3 (20.7 g, 0.15 mol) and dimethylsulfamoyl chloride (17.9 g, 0.125 mol) were added. The reaction mixture was stirred at room temperature for 16 hours. HPLC analysis showed the complete formation of 2,5,6-trichloro-benzoimidazole-1-sulfonic acid dimethylamide. In the same pot, without isolation of 2,5,6-trichloro-benzoimidazole-1-sulfonic acid dimethylamide, was added 1H-pyrazole-4-carboxylic acid ethyl ester (17.5 g, 0.125 mol) and K2CO3 (20.7 g, 0.15 mol). The reaction mixture was stirred at 70° C. for 4 hours and water (500 mL) was added while the reaction solution was still hot. The reaction solution was cooled to room temperature. The precipitated solid was collected via filtration, washed with water and dried. The crude product was used in the following reaction without further purification.

Workup

  1. stirringThe reaction mixture was stirred at 70° C. for 4 hours
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationThe precipitated solid was collected via filtration
  4. washwashed with water
  5. customdried
  6. customThe crude product was used in the following reaction without further purification

Sources & evidence

ORD record
ord-7f2785df47c34cf4aee56937e9e96496
Source dataset
uspto-grants-2016_03
Patent number
US09273034B2

Reaction notes

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