Hydrochloric Acid → HCID 3481508, compound

HRID 1417279Notes

Reaction equation

HRID 1417279 reaction equation
Br.[CH:2]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([NH2:19])[S:17][CH:18]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>N1C=CC=CC=1>[CH:2]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([NH:19][S:26]([C:23]4[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=4)(=[O:28])=[O:27])[S:17][CH:18]=3)=[CH:10][CH:9]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 21845593HCID 21845593, compound

Product 1

HCID 3481508HCID 3481508, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(4-cyclohexyl-phenyl)-thiazol-2-ylamine hydrobromide with 0.31 g of p-toluenesulfonyl chloride was stirred for 3 hours 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 ethyl acetate. 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 0.5 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 in amorphous form upon neutralization with concentrated hydrochloric acid. After chromatography on 70 g of Kieselgel 60 with ethyl acetate/hexane (1:2) the product-containing fractions were concentrated. Recrystallization from 50% ethanol yielded 0.22 g of N-[4-(4-cyclohexyl-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  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 0.5 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. customThe product separated in amorphous form upon neutralization with concentrated hydrochloric acid
  8. concentrationAfter chromatography on 70 g of Kieselgel 60 with ethyl acetate/hexane (1:2) the product-containing fractions were concentrated
  9. customRecrystallization from 50% ethanol

Sources & evidence

ORD record
ord-6d9379875b704400badaaaa2d95f1574
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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