Reaction #2254154

Reaction equation

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

Solvents

methylene chloride

methylene chloride

Conditions

Workup

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

Procedure

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