반응 #48204

반응 방정식

Sulphamoyl chloride

toluene

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

→

Sulfamic Acid 2-chloro-5-{[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-methyl}-phenyl Ester

용매

water

Ethyl acetate

N,N-dimethylacetamide

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타the organic layer was separated
3. 3
   세척washed with water (2×30 mL) and brine (20 mL)
4. 4
   건조dried over sodium sulphate
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in a small amount of acetone
7. 7
   기타precipitated by addition of diethyl ether and hexane
8. 8
   여과The precipitate was filtered off
9. 9
   기타dried under high vacuum

실험 절차

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-[(4-Chloro-3-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02141, 200 mg, 0.614 mmol) was added to the colourless solution and the mixture was stirred for 18 hours 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 diethyl ether and hexane. The precipitate was filtered off and dried under high vacuum. Yield: 136 mg (55%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=5.11 (s, 2H), 6.75 (d, J=9.0 Hz, 2H), 7.25 (dd, J=8.2, 2.0 Hz, 1H), 7.46 (d, J=2.0 Hz, 1H), 7.54 (d, J=8.2 Hz, 1H), 7.77 (d, J=9.0 Hz, 2H), 8.32 (s, 2H, —NH2), 8-82 (s, 2H). LRMS (FAB+): 87.0 (100), 404.9 (40, [M+H]+). HRMS (FAB+): 405.05338 C16H14N6O3SCl requires 405.053663.

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