Trifluoroacetic acid → HCID 19361479, compound

HRID 1417191Notes

Reaction equation

HRID 1417191 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 60. 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 and 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 60
  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
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-19333f1a0aa14fca8919b404d9b45559
Source dataset
uspto-grants-1999_03
Patent number
US05876756

Reaction notes

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