Реакция #48204

Уравнение реакции

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

Растворители

water

Ethyl acetate

N,N-dimethylacetamide

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Другоеthe organic layer was separated
3. 3
   Промывкаwashed with water (2×30 mL) and brine (20 mL)
4. 4
   Сушкаdried over sodium sulphate
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in a small amount of acetone
7. 7
   Другоеprecipitated by addition of diethyl ether and hexane
8. 8
   ФильтрацияThe precipitate was filtered off
9. 9
   Другоеdried under high vacuum

Методика

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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