Hydrochloric Acid → HCID 3919409, compound

HRID 619049Notes

Reaction equation

HRID 619049 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.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.Cl>N1C=CC=CC=1>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([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:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 21845604HCID 21845604, compound

Product 1

HCID 3919409HCID 3919409, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(1-naphthyl)-thiazol-2-ylamine hydrobromide with 0.34 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and extracted twice with 40 ml of ethyl acetate each time. The organic extracts were combined, 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 0.4 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 upon neutralization with concentrated hydrochloric acid. Recrystallization from 60 ml of 50% ethanol yielded 0.46 g of 4-methyl-N-(4-naphthalen-1-yl-thiazol-2-yl)-benzenesulfonamide as colorless crystals.

Workup

  1. extractionextracted twice with 40 ml of ethyl acetate each time
  2. dry with materialdried 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 0.4 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. customThe product separated upon neutralization with concentrated hydrochloric acid
  8. customRecrystallization from 60 ml of 50% ethanol

Sources & evidence

ORD record
ord-fa1bd783cad247d59e1645bdd7fff41a
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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