Toluene → HCID 86590099, compound

HRID 1072646Notes

Reaction equation

HRID 1072646 reaction equation
C[N:2]([C:4]([NH:6][C:7]([NH2:9])=[NH:8])=[NH:5])[CH3:3].[F:10][C:11]([F:34])([F:33])[C:12]([F:32])([F:31])[C:13]([F:30])([F:29])[C:14](OC(=O)C(F)(F)C(F)(F)C(F)(F)F)=[O:15].[C:35]1(C)C=CC=CC=1>>[F:31][C:12]([F:32])([C:11]([F:34])([F:33])[F:10])[C:13]([F:30])([F:29])[C:14]([N:2]([CH3:3])[C:4]([N:6]([CH3:35])[C:7](=[NH:8])[NH2:9])=[NH:5])=[O:15]

Participants

4

Reactant 3

HCID 1140TolueneHCID 67643Heptafluorobutyric anhydrideHCID 178484382HCID 178484382, compound

Product 1

HCID 86590099HCID 86590099, compound

Procedure

To a solution of metformin in dry toluene was slowly added heptafluorobutyric anhydride (1.2 equivalents) and stirred at ambient temperature for 4 hours. The reaction was terminated by addition of water and the reaction mixture was precipitated in acetone. The crude fluorinated metformin was chromatographed on silica gel, yielding N-heptafluorobutyryl N,N′-dimethylimidodicarbonimidic diamide.

Workup

  1. customThe reaction was terminated by addition of water
  2. customthe reaction mixture was precipitated in acetone
  3. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-b76fe96ddf514221afc7c872db428019
Source dataset
uspto-grants-2005_06
Patent number
US06911457B2

Reaction notes

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