Hydrochloric Acid → 3-Iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide

HRID 743029Notes

Reaction equation

HRID 743029 reaction equation
[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[I:9][C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1.Cl>C(C(C)=O)C(C)C>[I:9][C:10]1[CH:11]=[C:12]([S:16]([NH:8][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 153472-Amino-3-methylpyridineHCID 39766m-Iodobenzenesulphonyl chloride

Product 1

HCID 194233943-Iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

32.4 g 3-methyl-2-pyridinamine (32.4 g, 0.3 mol) was dissolved in isobutylmethylketone (200 ml) and 3-iodo-benzenesulfonyl chloride (30.2 g, 0.1 mol) was added with stirring. The solution was kept at 40° C. for 8 h and then added to dilute hydrochloric acid. The precipitate was filtered off and the organic phase was separated and evaporated. The residue was combined with the first solid material and recrystallized from ethanol. The crystals were dissolved in 1M sodium hydroxide (about 200? ml) and extracted with isobutylmethylketone (3×100 ml). The aqueous phase was partially evaporated to remove isobutylmethylketone residues. Ethanol (100? ml) was added and the solution acidified with acetic acid. The precipitate was filtered off, washed with water and dried. Yield 23 g, 61%.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe organic phase was separated
  3. customevaporated
  4. customrecrystallized from ethanol
  5. dissolutionThe crystals were dissolved in 1M sodium hydroxide (about 200? ml)
  6. extractionextracted with isobutylmethylketone (3×100 ml)
  7. customThe aqueous phase was partially evaporated
  8. customto remove isobutylmethylketone residues
  9. additionEthanol (100? ml) was added
  10. filtrationThe precipitate was filtered off
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-a33715cf014c4ed6a3ec12f3a1e0e152
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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