Hydrochloric Acid → HCID 21845608, compound

HRID 1417287Notes

Reaction equation

HRID 1417287 reaction equation
Br.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([NH2:21])[S:19][CH:20]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.Cl>N1C=CC=CC=1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([NH:21][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[S:19][CH:20]=2)=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 21845558HCID 21845558, compound

Product 1

HCID 21845608HCID 21845608, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(4-benzyloxy-phenyl)-thiazol-2-ylamine hydrobromide with 0.29 g of p-toluenesulfonyl chloride was stirred for 4 houtd with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and the mixture was extracted with methylene chloride. The organic phase was dried with magnesium sulphate and concentrated. The residue was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.7 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 and the residue was chromatographed on 100 g of Kieselgel 60 with diethyl ether as the eluent. The product-containing fractions were concentrated and, after recrystallization from ethyl acetate, yielded 0.22 g of N-[4-(4-benzyloxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as colorless crystals.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  5. additionAfter the addition of 0.7 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. concentrationAfter neutralization with concentrated hydrochloric acid the mixture was concentrated
  8. customthe residue was chromatographed on 100 g of Kieselgel 60 with diethyl ether as the eluent
  9. concentrationThe product-containing fractions were concentrated
  10. customafter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6a45d853ed97425a906021e634923fb6
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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