Hydrochloric Acid → 3,4-Dimethoxy-N-(4-naphthalen-2-yl-thiazol-2-yl)-benzenesulfonamide

HRID 619071Notes

Reaction equation

HRID 619071 reaction equation
Br.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([S:28](Cl)(=[O:30])=[O:29])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27].Cl>N1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([S:28]([NH:17][C:14]2[S:15][CH:16]=[C:12]([C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:2]=3)[N:13]=2)(=[O:29])=[O:30])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 28030374-(2-Naphthyl)-thiazol-2-ylamine hydrobromide

Product 1

HCID 218455843,4-Dimethoxy-N-(4-naphthalen-2-yl-thiazol-2-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 10 g of 4-(2-naphthyl)-thiazol-2-ylamine hydrobromide with 8.5 g of 3,4-dimethoxy-benzenesulfonyl chloride was stirred for 18 hours with 40 ml of pyridine. The resulting, red colored suspension was poured into 400 ml of 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and (sic) concentrated. The residue was dissolved in a mixture of 500 ml of ethanol and 400 ml of 2N sodium hydroxide solution. After the addition of 10 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. 11.1 g of 3,4-dimethoxy-N-(4-naphthalen-2-yl-thiazol-2-yl)-benzenesulfonamide separated upon neutralization with concentrated hydrochloric acid in the form of colorless crystals, which were recrystallized from ethanol/water.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried with magnesium sulphate and (sic)
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of 500 ml of ethanol and 400 ml of 2N sodium hydroxide solution
  5. additionAfter the addition of 10 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. custom11.1 g of 3,4-dimethoxy-N-(4-naphthalen-2-yl-thiazol-2-yl)-benzenesulfonamide separated upon neutralization with concentrated hydrochloric acid in the form of colorless crystals, which
  8. customwere recrystallized from ethanol/water

Sources & evidence

ORD record
ord-bbee4c462d214880889b749e23286c7e
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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