Hydrochloric Acid → HCID 21845569, compound

HRID 619029Notes

Reaction equation

HRID 619029 reaction equation
Br.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[N:13]=[C:14]([NH2:17])[S:15][CH:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[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>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[N:13]=[C:14]([NH:17][S:24]([C:21]3[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=3)(=[O:26])=[O:25])[S:15][CH:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 21845589HCID 21845589, compound

Product 1

HCID 21845569HCID 21845569, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(3,4-dimethoxy-phenyl)-thiazol-2-ylamine hydrobromide with 0.33 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored solution was poured into 50 ml of 1N hydrochloric acid and extracted three times with 50 ml of methylene chloride each time. The organic extracts were combined, dried with magnesium sulphate and concentrated. The residue was chromatographed on 35 g of Kieselgel 60 with diethyl ether as the eluent. The product-containing fractions were concentrated, dissolved in 40 ml of 50% ethanol by the addition of a small amount of 2N sodium hydroxide solution and precipitated with 2N hydrochloric acid at pH 6. 0.4 g of N-[4-(3,4-dimethoxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide was obtained as colorless crystals.

Workup

  1. extractionextracted three times with 50 ml of methylene chloride each time
  2. dry with materialdried with magnesium sulphate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on 35 g of Kieselgel 60 with diethyl ether as the eluent
  5. concentrationThe product-containing fractions were concentrated
  6. dissolutiondissolved in 40 ml of 50% ethanol by the addition of a small amount of 2N sodium hydroxide solution
  7. customprecipitated with 2N hydrochloric acid at pH 6

Sources & evidence

ORD record
ord-2823f480e7824be1b0f29732f0d2b848
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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