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

HRID 1417259Notes

Reaction equation

HRID 1417259 reaction equation
Br.[Br: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>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([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:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 27878804-(4-Bromophenyl)-1,3-thiazol-2-amine hydrobromide

Product 1

HCID 3547779N-[4-(4-Bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.0 g of 4-(4-bromophenyl)-thiazol-2-ylamine hydrobromide with 2.5 g of p-toluenesulfonyl chloride was stirred overnight with 15 ml of pyridine. The resulting, red colored suspension was poured into 180 ml of 1N hydrochloric acid and the solid which thereby separated was filtered off and chromatographed on 100 g of Kieselgel 60 with diethyl ether/hexane/methylene chloride (1:1:1) as the eluent. The product-containing fractions were concentrated and the residue was recrystallized twice from 60% ethanol. 0.8 g of N-[4-(4-bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide separated as colorless crystals upon cooling.

Workup

  1. customthe solid which thereby separated
  2. filtrationwas filtered off
  3. customchromatographed on 100 g of Kieselgel 60 with diethyl ether/hexane/methylene chloride (1:1:1) as the eluent
  4. concentrationThe product-containing fractions were concentrated
  5. customthe residue was recrystallized twice from 60% ethanol
  6. custom0.8 g of N-[4-(4-bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide separated as colorless crystals
  7. temperatureupon cooling

Sources & evidence

ORD record
ord-d744be941c064901a46ef9ddb1008d63
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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