Toluene → 4-{[Bis-(4-sulphamoyloxy-phenyl)-methyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

HRID 19949

Reaktionsgleichung

Reaktionsgleichung von HRID 19949
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([N:28]([N:37]2[CH:41]=[N:40][N:39]=[CH:38]2)[C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1>C(OCC)(=O)C.O.CN(C)C(=O)C>[S:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([N:28]([N:37]2[CH:41]=[N:40][N:39]=[CH:38]2)[C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[C:21]2[CH:26]=[CH:25][C:24]([O:27][S:1](=[O:4])(=[O:3])[NH2:2])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)(=[O:4])(=[O:3])[NH2:2]

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219768584-([Bis-(4-hydroxy-phenyl)-methyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Produkt 1

HCID 219768864-{[Bis-(4-sulphamoyloxy-phenyl)-methyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel2×HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Sulphamoyl chloride solution in toluene (5 mL, 0.7 M, 3.5 mmol) was concentrated under reduced pressure (30° C. water bath temperature) to ca. 1 mL volume. The residue was cooled to 0° C. (ice bath) and N,N-dimethylacetamide (5 mL) was added. 4-{[Bis-(4-hydroxy-phenyl)-methyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB2070, 250 mg, 0.65 mmol) was added to the colourless solution and the mixture was stirred for 18 h at, room temperature. Ethyl acetate (50 mL) and water (30 mL) were added to the solution, the organic layer was separated, washed with water (2×30 mL) and brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure to give a white solid. The solid was dissolved in ethyl acetate and precipitated by addition of hexane. The white powder was filtered off and dried under high vacuum. Yield: 299 mg (85%).

Aufarbeitung

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×30 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto give a white solid
  7. customprecipitated by addition of hexane
  8. filtrationThe white powder was filtered off
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3a71e3aaa6c843ed9a29a7fb1e9c4aea
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745472B2

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