HCID 9837522, Verbindung → HCID 10522547, Verbindung

HRID 1417246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417246
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]([NH2:13])=[S:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=1)=O>C(O)C>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:13]=[C:11]([NH:10][S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:14])=[CH:6][CH:5]=3)(=[O:9])=[O:8])[S:12][CH:16]=2)=[CH:20][C:21]=1[CH3:26]

Komponenten

4

Edukt 2

HCID 9837522HCID 9837522, VerbindungHCID 112184492-Bromo-1-(4-hydroxy-3-methylphenyl)ethanone

Produkt 1

HCID 10522547HCID 10522547, VerbindungAusbeute 24,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 26 g of 4-toluenesulfonyl-thiourea in 225 ml of ethanol was treated with 25.9 g of 2-bromo-1-(4-hydroxy-3-methyl-phenyl)-ethanone, left to stand at room temperature for 3 days and then boiled for a brief period. The reaction mixture was evaporated to dryness in a vacuum and subsequently partitioned between water and ethyl acetate. The aqueous phase was extracted once with ethyl acetate, the organic phases were combined, dried with sodium sulphate and concentrated. The residue was chromatographed on 500 g of Kieselgel 60 with ethyl acetate/hexane (1:1) as the eluent. The product-containing fractions were concentrated and, after recrystallization from 50% ethanol, yielded 10.1 g of N-[4-(4-hydroxy-3-methyl-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as colourless crystals.

Aufarbeitung

  1. waitleft
  2. waitboiled for a brief period
  3. customThe reaction mixture was evaporated to dryness in a vacuum
  4. customsubsequently partitioned between water and ethyl acetate
  5. extractionThe aqueous phase was extracted once with ethyl acetate
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on 500 g of Kieselgel 60 with ethyl acetate/hexane (1:1) as the eluent
  9. concentrationThe product-containing fractions were concentrated
  10. customafter recrystallization from 50% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0dc488b3c19f40af812c3560a206ebca
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877193

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