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

HRID 619040

Reaction equation

HRID 619040 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].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].Cl>N1C=CC=CC=1>[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([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:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 28704454-(3-Nitro-phenyl)-thiazol-2-ylamine hydrobromide

Product 1

HCID 107636944-Isopropyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamideYield 25.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.36 g of 4-isopropylbenzenesulfonyl 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 organic phase was separated 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. The product separated as an oil upon neutralization. Thereupon, the mixture was boiled with 0.5 g of active charcoal and the active charcoal and insoluble constituents were filtered off. Crystals separated upon cooling and, after recrystallization from 40 ml of 50% ethanol, yielded 0.17 g of 4-isopropyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as colourless crystals.

Workup

  1. customthe organic phase was separated
  2. dissolutiondissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  3. additionAfter the addition of 0.5 g of active charcoal the mixture
  4. filtrationsubsequently the active charcoal was filtered off
  5. customThe product separated as an oil upon neutralization
  6. filtrationthe active charcoal and insoluble constituents were filtered off
  7. customCrystals separated
  8. temperatureupon cooling
  9. customafter recrystallization from 40 ml of 50% ethanol

Sources & evidence

ORD record
ord-d784e64d8f8d4f339818fa2f6f827ec4
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Linked notes

Loading…