1,1'-sulphonylbis-1H-imidazole → 4-Amino-5-ethoxy-1,2,3-benzoxathiazine 2,2-dioxide

HRID 1920713Notes

Reaction equation

HRID 1920713 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[C:11](=[NH:13])[NH2:12])[CH3:2].[S:14](N1C=CN=C1)(N1C=CN=C1)(=[O:16])=[O:15]>O>[NH2:13][C:11]1[C:5]2[C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=2[O:10][S:14](=[O:16])(=[O:15])[N:12]=1

Participants

4

Reactant 2

HCID 816091,1'-sulphonylbis-1H-imidazoleHCID 1360739132-Ethoxy-6-hydroxybenzenecarboximidamide

Product 1

HCID 462386994-Amino-5-ethoxy-1,2,3-benzoxathiazine 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.25 g (1.39 mmol) of 2-ethoxy-6-hydroxybenzenecarboximidamide is stirred without solvent with 0.65 g (3.28 mmol) of 1,1′-sulphonyldiimidazole at 130° C. for 18 hours. Cooling is followed by stirring the mixture with water and removing with dichloromethane. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. This gives 0.2 g of a pale yellow, crystalline material.

Workup

  1. temperatureCooling
  2. customremoving with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db444358b5064ccea948f1c2d8203590
Source dataset
uspto-grants-2012_05
Patent number
US08173641B2

Reaction notes

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