Hydrochloric Acid → HCID 21845602, compound

HRID 1417294Notes

Reaction equation

HRID 1417294 reaction equation
Br.[C:2]1([C:12]2[N:13]=[C:14]([NH2:17])[S:15][CH:16]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>N1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:17][C:14]2[S:15][CH:16]=[C:12]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[CH:4][CH:3]=3)[N:13]=2)(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 21845604HCID 21845604, compound

Product 1

HCID 21845602HCID 21845602, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 10 g of 4-(1-naphthyl)-thiazol-2-ylamine hydrobromide with 7.4 g of 4-methoxy-benzenesulfonyl chloride was stirred for 16 hours with 40 ml of pyridine. The resulting, red colored suspension was poured into 400 ml of 1N hydrochloric acid and the extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulphate and free from solvent. 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. After neutralization with concentrated hydrochloric acid the mixture was concentrated, the residue was taken up with ethyl acetate, dried with magnesium sulphate and concentrated. Crystallization from ethyl acetate/hexane yielded 10.2 g of 4-methoxy-N-(4-naphthalen-1-yl-thiazol-2-yl)-benzenesulfonamide as colorless crystals, which were recrystallized once from ethyl acetate/hexane.

Workup

  1. extractionthe extracted with ethyl acetate
  2. dry with materialdried with magnesium sulphate and free from solvent
  3. dissolutionThe residue was dissolved in a mixture of 500 ml of ethanol and 400 ml of 2N sodium hydroxide solution
  4. additionAfter the addition of 10 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. concentrationAfter neutralization with concentrated hydrochloric acid the mixture was concentrated
  7. dry with materialdried with magnesium sulphate
  8. concentrationconcentrated
  9. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ce13f111e8ca4dfdb10f524e9ecb9f4f
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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