Hydrochloric Acid → 4-Methyl-N-[4-(2-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 1417270Notes

Reaction equation

HRID 1417270 reaction equation
Br.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1)([O-:4])=[O:3].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>N1C=CC=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:16][C:13]2[S:14][CH:15]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N+:2]([O-:4])=[O:3])[N:12]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 218455924-(2-Nitro-phenyl)-thiazol-2-ylamine hydrobromide

Product 1

HCID 218455994-Methyl-N-[4-(2-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(2-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.47 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 extracted twice with 40 ml of ethyl acetate each time. The organic extracts were combined, dried with magnesium sulphate and concentrated. The residue was dissolved in a mixture of 30 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. After neutralization with concentrated hydrochloric acid and boiling there separated, upon cooling, 0.58 g of 4-methyl-N-[4-(2-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as yellow crystals.

Workup

  1. extractionextracted twice with 40 ml of ethyl acetate each time
  2. dry with materialdried with magnesium sulphate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of 30 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. customAfter neutralization with concentrated hydrochloric acid and boiling there separated
  8. temperatureupon cooling

Sources & evidence

ORD record
ord-e3563b45dbd14165bc552a49d9cabeae
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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