Hydrochloric Acid → 3,4-Dichloro-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 1417255Notes

Reaction equation

HRID 1417255 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[Cl:17][C:18]1[CH:19]=[C:20]([S:25](Cl)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[Cl:24].Cl>N1C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[C:20]([S:25]([NH:16][C:13]2[S:14][CH:15]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=3)[N:12]=2)(=[O:26])=[O:27])[CH:21]=[CH:22][C:23]=1[Cl:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 218455864-(3-Nitrophenyl)thiazol-2-amine hydrochloride

Product 1

HCID 105266133,4-Dichloro-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamideYield 46.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrochloride with 0.52 g of 3,4-dichlorobenzenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 25 ml of 1N hydrochloric acid and the solid which thereby separated was filtered off and dissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.5 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 80 ml of 50% ethanol yielded 0.39 g of 3,4-dichloro-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as yellowish crystals.

Workup

  1. customthe solid which thereby separated
  2. filtrationwas filtered off
  3. dissolutiondissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  4. additionAfter the addition of 0.5 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. customThe product separated upon neutralization with concentrated hydrochloric acid
  7. customRecrystallization from 80 ml of 50% ethanol

Sources & evidence

ORD record
ord-4835c459a5c9462789741a5038e4c768
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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