Hydrochloric Acid → N-[4-(4-Methoxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

HRID 619045Notes

Reaction equation

HRID 619045 reaction equation
Br.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([NH:15][S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[S:13][CH:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 164648644-(4-Methoxy-phenyl)-thiazol-2-ylamine; hydrobromide

Product 1

HCID 2400649N-[4-(4-Methoxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamideYield 38.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(4-methoxy-phenyl)-thiazol-2-ylamine hydrobromide with 0.37 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and the mixture was extracted twice with 40 ml of ethyl acetate each time. The organic phases were combined, dried with magnesium sulphate and the solvent was removed on a rotary evaporator. The residue was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.4 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 30 ml of 50% ethanol yielded 0.24 g of N-[4-(4-methoxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as beige crystals.

Workup

  1. extractionthe mixture was extracted twice with 40 ml of ethyl acetate each time
  2. dry with materialdried with magnesium sulphate
  3. customthe solvent was removed on a rotary evaporator
  4. dissolutionThe residue was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  5. additionAfter the addition of 0.4 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. customThe product separated upon neutralization with concentrated hydrochloric acid
  8. customRecrystallization from 30 ml of 50% ethanol

Sources & evidence

ORD record
ord-4e5b7422bd0a4ab0ac4cfcd7e87397e3
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

Loading…