Hydrochloric Acid → 4-methyl-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide

HRID 1417269Notes

Reaction equation

HRID 1417269 reaction equation
Br.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:14])[S:12][CH:13]=2)=[CH:5][CH:4]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Cl>N1C=CC=CC=1>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:14][C:11]2[S:12][CH:13]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH3:2])=[CH:8][CH:7]=3)[N:10]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 168247844-p-Tolyl-thiazol-2-ylamine hydrobromide

Product 1

HCID 8978414-methyl-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamideYield 72.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g 4-(4-methyl-phenyl)-thiazol-2-ylamine hydrobromide with 0.39 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 50 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. 0.46 g of 4-methyl-N-[4-(4-methyl-phenyl)-thiazol-2-yl]-benzenesulfonamide was obtained as colorless crystals upon neutralization with concentrated hydrochloric acid.

Workup

  1. extractionthe mixture was extracted twice with 50 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

Sources & evidence

ORD record
ord-4ced5fa976d1406fbad6b37124e4ddc4
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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