4-Bromo-2-iodoaniline → Benzothiazole, 6-bromo-2-methyl-

HRID 1270893

Reaktionsgleichung

Reaktionsgleichung von HRID 1270893
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4](I)[CH:3]=1.[CH3:10][C:11](N)=[S:12]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:11]([CH3:10])[S:12][C:4]=2[CH:3]=1

Komponenten

6

Edukt 2

HCID 8239344-Bromo-2-iodoanilineHCID 2723949Thioacetamide

Produkt 1

HCID 138448Benzothiazole, 6-bromo-2-methyl-Ausbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-2-iodo-phenylamine (1.5 g, 5.0 mmol), thiacetamide (381 mg, 5.0), cupric oxide (280 mg, 3.5 mmol), dppf (56 mg, 0.10 mmol), Pd2(dba)3 (48 mg, 0.052 mmol) in DMF was heated at 60° C. for 1 hour, cooled to room temperature, partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and concentrated. The concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride to give 550 mg (40% yield) of the desired product. MS (ESI(+)) m/e 227.8, 229.8 (M+H)+.

Aufarbeitung

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-336ac4bd754845cdb389cffd63b7f993
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202363B2

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