Trifluoromethanesulfonic anhydride → HCID 54073776, compound

HRID 359254Notes

Reaction equation

HRID 359254 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:16][O:17][C:18]([C:20]1[N:24]([CH:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([CH3:35])(O)[C:26]2([CH3:37])[CH3:36])[CH:23]=[N:22][CH:21]=1)=[O:19]>N1C=CC=CC=1>[CH3:16][O:17][C:18]([C:20]1[N:24]([CH:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](=[CH2:35])[C:26]2([CH3:37])[CH3:36])[CH:23]=[N:22][CH:21]=1)=[O:19]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 54226953HCID 54226953, compound

Product 1

HCID 54073776HCID 54073776, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.7 ml of trifluoromethanesulfonic acid anhydride are added dropwise at a temperature of -15° C. to a solution of 2.5 g of 1-(2,2,3-trimethyl-3-hydroxyindan-1-yl)-5-imidazolecarboxylic acid methyl ester in 20 ml of pyridine. After a reaction period of 10 minutes the mixture is concentrated by evaporation in vacuo and the residue is chromatographed on silica gel using an ether/methylene chloride mixture (1:1). 1.2 g of 1-(2,2-dimethyl-3-methylideneindan-1-yl)-5-imidazolecarboxylic acid methyl ester are obtained in the form of brownish colourless crystals having a melting point of 125°-126° C.

Workup

  1. customAfter a reaction period of 10 minutes the mixture
  2. concentrationis concentrated by evaporation in vacuo
  3. customthe residue is chromatographed on silica gel using an ether/methylene chloride mixture (1:1)

Sources & evidence

ORD record
ord-3150ca195f254cf2a1ea0b52b4aeac84
Source dataset
uspto-grants-1991_03
Patent number
US05000777

Reaction notes

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