Trifluoroacetate → HCID 11644225, compound

HRID 749154Notes

Reaction equation

HRID 749154 reaction equation
C([O:8][C:9]1[C:10]([O:22][CH3:23])=[CH:11][C:12]([C:20]#[N:21])=[C:13]([N:15]=[CH:16][N:17]([CH3:19])[CH3:18])[CH:14]=1)C1C=CC=CC=1.FC(F)(F)C([O-])=O>FC(F)(F)C(O)=O>[C:20]([C:12]1[CH:11]=[C:10]([O:22][CH3:23])[C:9]([OH:8])=[CH:14][C:13]=1[N:15]=[CH:16][N:17]([CH3:18])[CH3:19])#[N:21]

Participants

4

Reactant 2

HCID 84468TrifluoroacetateHCID 11609261N'-(2-cyano-4-methoxy-5-benzyloxyphenyl)-N,N-dimethylimidoformamide

Product 1

HCID 11644225HCID 11644225, compoundYield 143.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N′-(5-(benzyloxy)-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide (110 g, 356 mmol) and trifluoroacetic acid (600 ml) were heated at reflux for 15 minutes. The reaction was evaporated in vacuo and then azeotroped with toluene. The residue was triturated with diethyl ether and the solid collected by suction filtration. The solid was dried in vacuo to yield N′-(2-cyano-5-hydroxy-4-methoxyphenyl)-N,N-dimethylimidoformamide (112 g, 95% yield) as a light brown trifluoroacetate salt:

Workup

  1. temperatureat reflux for 15 minutes
  2. customThe reaction was evaporated in vacuo
  3. customazeotroped with toluene
  4. customThe residue was triturated with diethyl ether
  5. filtrationthe solid collected by suction filtration
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-8a869765dbcb467a889d03b02e323494
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

Loading…