Reaktion #1159390

Reaktionsgleichung

water

methanesulfonyl chloride

5-amino-2,3,4,5-tetrahydro-1-benzoxepine

triethylamine

→

5-methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine

Ausbeute 74.7%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto come to RT
2. 2
   workup.DISTILLATIONthe THF was distilled off in vacuo
3. 3
   workup.ADDITIONThe residue was diluted with a further 50 ml of water
4. 4
   workup.STIRRINGstirred for 3 h
5. 5
   Filtrationthe deposited product was filtered off with suction
6. 6
   SonstigeAfter drying in vacuo

Vorschrift

1.54 g (13.4 mmol) of methanesulfonyl chloride were added dropwise with ice cooling to a solution of 2.0 g (12.2 mmol) of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine (Example 6b) and 3.7 g (36.6 mmol triethylamine in 40 ml of THF. The mixture was allowed to come to RT and was stirred overnight and treated with 50 ml of water, and the THF was distilled off in vacuo. The residue was diluted with a further 50 ml of water and stirred for 3 h, and the deposited product was filtered off with suction. After drying in vacuo, 2.2 g of 5-methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine were obtained, m.p. 105-106° C. b) A solution of 1.1 g (6.2 mmol) of 5-methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine in 15 ml of THF was added dropwise to a suspension of 0.23 g (6.2 mmol) of 80 percent sodium hydride in 10 ml of THF. After 2 h at RT, 0.94 g (6.7 mmol) of iodomethane were added and the mixture was stirred overnight at RT. After distilling off the solvent in vacuo, the residue was taken up in EA, and the solution was washed with dilute hydrochloric acid and water, dried over magnesium sulfate and concentrated. Subsequent recrystallization of the product from isopropanol yielded 0.5 g of 5-(N-methyl-N-methylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine, m.p. 143-145° C.

Quelle