Benzenesulfonamide, N-(((4,6-dimethyl-2-pyrimidinyl)amino)carbonyl)-2-nitro- → HCID 13138213, compound

HRID 1262798Notes

Reaction equation

HRID 1262798 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)(=[O:15])=[O:14])=[O:11])[N:3]=1.[H][H]>[Pd].C(O)C>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:10]([NH:9][C:4]1[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)=[O:11])(=[O:14])=[O:15]

Participants

5

Reactant 2

HCID 155933Benzenesulfonamide, N-(((4,6-dimethyl-2-pyrimidinyl)amino)carbonyl)-2-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 13138213HCID 13138213, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension containing 1 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide, 0.2 g of 5% palladium on carbon and 50 ml of ethanol was shaken in a Paar apparatus under 40 p.s.i.g. hydrogen at ambient temperature. After one hour, the reaction mixture was filtered and the solids thereby recovered, which contained catalyst and desired product, was stirred with 10% aqueous sodium hydroxide. Filtration of that mixture and acidification of the filtrate with hydrochloric acid to pH 3 caused the desired product to precipitate. After removal by filtration and drying, the desired product melted at 212°-216° and showed infrared absorption peaks at 3200 and 3300 cm-1, consistent for the desired amino-containing compound. Mass spectrometry showed two particles of mass 198 and 123 units, equivalent to aminobenzenesulfonyl isocyanate and 2-amino-4,6-dimethylpyrimidine respectively, as expected for the desired compound.

Workup

  1. customat ambient temperature
  2. filtrationthe reaction mixture was filtered
  3. customthe solids thereby recovered
  4. stirringwas stirred with 10% aqueous sodium hydroxide
  5. filtrationFiltration of that mixture and acidification of the filtrate with hydrochloric acid to pH 3
  6. customto precipitate
  7. customAfter removal
  8. filtrationby filtration
  9. customdrying
  10. customabsorption peaks at 3200 and 3300 cm-1
  11. additionconsistent for the desired amino-containing compound

Sources & evidence

ORD record
ord-2083f94ce35c4a5794fa4b6a62e9ad78
Source dataset
uspto-grants-1984_06
Patent number
US04453971

Reaction notes

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