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Potassium Carbonate → N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide

HRID 619082
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 619082
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:13]([CH2:24][O:25][CH3:26])[S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[Li+].[C:29]1(OB(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:2]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[N:9]=[C:10]([N:13]([CH2:24][O:25][CH3:26])[S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[S:11][CH:12]=2)[CH:3]=1
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Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 433294Lithium ChlorideHCID 21845556N-[4-(3-bromo-phenyl)-thiazol-2-yl]-N-methoxymethyl-4-methyl-benzenesulfonamide

Produkt 1

HCID 21845572N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 0.5 g of N-[4-(3-bromo-phenyl)-thiazol-2-yl]-N-methoxymethyl-4-methyl-benzenesulfonamide in 8 ml of toluene was treated in succession with 0.1 g of anhydrous lithium chloride, 60 mg of tetrakis(triphenylphosphine)palladium, 0.23 g of phenylboric acid and 2 ml of 2N potassium carbonate solution. The mixture was boiled overnight, cooled and, after the addition of water, extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulphate and concentrated. The residue was chromatographed on 80 g of Kieselgel 60 with ethyl acetate/hexane (1:4) as the eluent. The product-containing fractions were concentrated and yielded 0.29 g of colorless, amorphous N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide, which was processed without further purification.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on 80 g of Kieselgel 60 with ethyl acetate/hexane (1:4) as the eluent
  6. concentrationThe product-containing fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4d7efd058c034afe930e4dfbea136566
Quelldatensatz
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05958910

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