Reaktion #48199

Reaktionsgleichung

Sulphamoyl chloride

toluene

4-[(3-Chloro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

→

Sulfamic Acid 2-chloro-4-{[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-methyl}-phenyl Ester

Lösungsmittel

water

Ethyl acetate

N,N-dimethylacetamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethe organic layer was separated
3. 3
   Waschenwashed with water (2×30 mL) and brine (20 mL)
4. 4
   Trocknendried over sodium sulphate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in a small amount of acetone
7. 7
   Sonstigeprecipitated by addition of hexane
8. 8
   FiltrationThe precipitate was filtered off
9. 9
   Sonstigedried under high vacuum

Vorschrift

Sulphamoyl chloride solution in toluene (3 mL, 0.7 M, 2.1 mmol) was concentrated under reduced pressure (30° C. water bath temperature) to ca 0.5 mL volume. The residue was cooled to 0° C. (ice bath) and N,N-dimethylacetamide (5 mL) was added. 4-[(3-Chloro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02130, 163 mg, 0.50 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. The residue was dissolved in a small amount of acetone and precipitated by addition of hexane. The precipitate was filtered off and dried under high vacuum. Yield: 59 mg (29%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=5.11 (5, 2H), 6.72 (d, J=9.0 Hz, 2H), 7.38 (dd, J=8.2, 2.0 Hz, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.59 (d, J=2.0 Hz, 1H), 7.77 (d, J=9.0 Hz, 2H), 8.31 (s, 2H, —NH2), 8.91 (s, 2H). LRMS (FAB+): 405.0 (100, [M+H]+). HRMS (FAB+) 405.05349 C16H14N6O3SCl requires 405.053663

Quelle