Trifluoroacetic acid → HCID 19361479, compound

HRID 376545Notes

Reaction equation

HRID 376545 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][OH:14])=[NH:12])=[CH:6][CH:5]=1)([OH:3])=[O:2].[F:15][C:16]([F:21])([F:20])[C:17](O)=O>O1CCCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:12]=[C:17]([C:16]([F:21])([F:20])[F:15])[O:14][N:13]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178513436HCID 178513436, compound

Product 1

HCID 19361479HCID 19361479, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In 100 ml of tetrahydrofuran was dissolved 4.0 g of N-(4-carboxyphenyl)-N'-hydroxyguanidine produced in Reference Example 27. To the solution was added, while stirring at 0° C., 6.75 g of anhydrous trifluoroacetic acid. The mixture was stirred for 1.5 hour under the same conditions, followed by concentration under reduced pressure. To the concentrate was added water. The resulting crystalline product was collected by filtration, which was recrystallized from ethyl acetate--hexane to afford 3.5 g of the title compound as a colorless crystalline product.

Workup

  1. customproduced in Reference Example 27
  2. additionTo the solution was added
  3. stirringThe mixture was stirred for 1.5 hour under the same conditions
  4. concentrationfollowed by concentration under reduced pressure
  5. additionTo the concentrate was added water
  6. filtrationThe resulting crystalline product was collected by filtration, which
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a10eef013dd948c98ccf1d8ed609e373
Source dataset
uspto-grants-2000_02
Patent number
US06020334

Reaction notes

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