1,1'-sulphonylbis-1H-imidazole → N-methyl-4-amino-1,2,3-benzoxathiazine 2,2-dioxide

HRID 1920714Notes

Reaction equation

HRID 1920714 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[NH:11])[NH:9][CH3:10].[S:12](N1C=CN=C1)(N1C=CN=C1)(=[O:14])=[O:13]>O>[CH3:10][N:9]1[CH:8]([NH2:11])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1][S:12]1(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 816091,1'-sulphonylbis-1H-imidazoleHCID 178484908HCID 178484908, compound

Product 1

HCID 67159524N-methyl-4-amino-1,2,3-benzoxathiazine 2,2-dioxideYield 33.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.18 g (1.20 mmol) of 2-hydroxyl-N-methylbenzenecarboximidamide is stirred with 0.48 g (2.42 mmol) of 1,1′-sulphonyldiimidazole at 120° C. for 18 hours. Cooling is followed by stirring the mixture with water and then decanting off from the water. The remaining residue is chromatographed on silica gel (450 g, 40-63 μm) with dichloromethane/methanol=99/1. 87 mg of product are isolated.

Workup

  1. temperatureCooling
  2. customdecanting off from the water
  3. customThe remaining residue is chromatographed on silica gel (450 g, 40-63 μm) with dichloromethane/methanol=99/1

Sources & evidence

ORD record
ord-907c667629ce4962b5d60cbf69b58a04
Source dataset
uspto-grants-2012_05
Patent number
US08173641B2

Reaction notes

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