Hydrochloric Acid → N-[4-(3-Bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

HRID 619052Notes

Reaction equation

HRID 619052 reaction equation
Br.[Br:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([NH2:14])[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=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>[Br:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([NH:14][S:21]([C:18]3[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=3)(=[O:23])=[O:22])[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 218456014-(3-Bromophenyl)-1,3-thiazol-2-amine hydrobromide

Product 1

HCID 21845574N-[4-(3-Bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(3-bromo-phenyl)-thiazol-2-ylamine hydrobromide with 0.31 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 solid which thereby separated was filtered off and 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. 0.40 g of N-[4-(3-bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide separated as colorless crystals upon neutralization with concentrated hydrochloric acid.

Workup

  1. customthe solid which thereby separated
  2. filtrationwas filtered off
  3. dissolutiondissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  4. additionAfter the addition of 0.4 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. custom0.40 g of N-[4-(3-bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide separated as colorless crystals upon neutralization with concentrated hydrochloric acid

Sources & evidence

ORD record
ord-1e3b450f11f946e7afbfa70638a7132a
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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