Hydrochloric Acid → N-{4-[4-(3-Nitro-phenyl)-thiazol-2-ylsulphamoyl]-phenyl}-acetamide

HRID 1417264Notes

Reaction equation

HRID 1417264 reaction equation
Br.[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].[NH:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:18]([CH3:20])=[O:19].Cl>N1C=CC=CC=1>[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH:16][S:27]([C:24]3[CH:23]=[CH:22][C:21]([NH:17][C:18](=[O:19])[CH3:20])=[CH:26][CH:25]=3)(=[O:29])=[O:28])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8481N-Acetylsulfanilyl chlorideHCID 28704454-(3-Nitro-phenyl)-thiazol-2-ylamine hydrobromide

Product 1

HCID 21845562N-{4-[4-(3-Nitro-phenyl)-thiazol-2-ylsulphamoyl]-phenyl}-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.43 g of 4-acetamino-benzenesulfonyl 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 0.5 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. 0.60 g of N-{4-[4-(3-nitro-phenyl)-thiazol-2-ylsulphamoyl]-phenyl}-acetamide separated as yellowish 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 0.5 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. custom0.60 g of N-{4-[4-(3-nitro-phenyl)-thiazol-2-ylsulphamoyl]-phenyl}-acetamide separated as yellowish crystals upon neutralization with concentrated hydrochloric acid

Sources & evidence

ORD record
ord-23ca7683db41488482d7799e4c3ea443
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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