Réaction #2254154

Équation de réaction

S,S-Diisopropyl-S-aminosulfonium 2,4,6-trimethyl-phenylsulfonate

6,8-dichloro-1H-benzo[d][1,3]oxazine-2,4-dione

Water

potassium tert-butanolate

→

title compound

2-amino-N-(bis-2-propyl-λ4-sulfanylidene)-3,5-dichloro-benzamide

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autreto come to room temperature
2. 2
   Autrethe organic phase was separated
3. 3
   Extractionthe aqueous phase further extracted with methylene chloride (2×100 mL)
4. 4
   SéchageThe combined organic extracts were dried (MgSO4)
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

To a suspension of 6,8-dichloro-1H-benzo[d][1,3]oxazine-2,4-dione (45.0 g, 70.7 mmol) in methylene chloride (500 mL) was added S,S-Diisopropyl-S-aminosulfonium 2,4,6-trimethyl-phenylsulfonate (77.6 g, 234 mmol). The reaction mixture was cooled to 0° C. and potassium tert-butanolate (8.73 g, 77.8 mmol) was added after which the reaction was allowed to come to room temperature and stirred for 16 h. Water (200 mL) and methylene chloride (50 mL) were then added, the organic phase was separated and the aqueous phase further extracted with methylene chloride (2×100 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound (62.8 g, quant.).

Source