Trifluoroacetic acid → HCID 19361479, compound

HRID 1585092Notes

Reaction equation

HRID 1585092 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-28b59d92e55f43db87bc3be69b760a21
Source dataset
uspto-grants-1999_08
Patent number
US05935963

Reaction notes

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