Water → HCID 86720241, compound

HRID 2166972Notes

Reaction equation

HRID 2166972 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:5]2[NH:6]C(=O)O[C:9](=[O:10])[C:4]=2[CH:3]=1.CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[CH:28]([S+:31]([CH:33]([CH3:35])[CH3:34])[NH2:32])([CH3:30])[CH3:29].C([O-])(C)(C)C.[K+].O>C(Cl)Cl>[NH2:6][C:5]1[C:12]([Cl:14])=[CH:13][C:2]([Cl:1])=[CH:3][C:4]=1[C:9]([N:32]=[S:31]([CH:33]([CH3:35])[CH3:34])[CH:28]([CH3:30])[CH3:29])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 784136,8-Dichloro-2H-3,1-benzoxazine-2,4(1H)-dioneHCID 23665647Potassium tert-butoxideHCID 86720242HCID 86720242, compound

Product 1

HCID 86720241HCID 86720241, compoundYield 276.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

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.).

Workup

  1. customto come to room temperature
  2. customthe organic phase was separated
  3. extractionthe aqueous phase further extracted with methylene chloride (2×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8cd3830461cc476896c7180c97132376
Source dataset
uspto-grants-2015_06
Patent number
US09044016B2

Reaction notes

Loading…