Potassium Carbonate → HCID 58748359, compound

HRID 1040580Notes

Reaction equation

HRID 1040580 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH3:12])(=[O:10])=[O:9].[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([Cl:21])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:13][C:14]1[N:19]=[C:18]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[C:17]([Cl:21])=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 11328402-amino-N-methylbenzene-1-sulfonamide

Product 1

HCID 58748359HCID 58748359, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2-amino-N-methyl-benzenesulfonamide (2.93, 15.75 mmol), 2,4,5 trichloropyrimidine (2.9 g, 15.84 mmol) and K2CO3 (4.5 g, 32.6 mmol) in dry DMF (25 mL) was stirred at 45° C. for 15 h. The solvent was removed and the residue was taken in water and was extracted twice from ethylacetate. Combined organic was washed with water and brine. After drying solvent was removed. Upon triturating with ether and filtration gave the product 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzenesulfonamide 7 as a white solid (2.6 g, 50%); 1H NMR (400 MHz, CDCl3) δ9.61 (s, 1H), 8.6 (d=12.89 Hz, 1H), 8.53 (s, 1H), 8.27 (s, 1H), 7.68 (m, 1H), 7.27 (m, 1H0, 1.66 (br s, 1H0, 2.66 (s, 3H).

Workup

  1. customThe solvent was removed
  2. extractionwas extracted twice from ethylacetate
  3. washCombined organic was washed with water and brine
  4. customAfter drying solvent
  5. customwas removed
  6. filtrationUpon triturating with ether and filtration

Sources & evidence

ORD record
ord-ec1f0aac33c74e64bcaf031dbb08c3f9
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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