Trifluoroacetic acid → HCID 53693452, compound

HRID 1493612Notes

Reaction equation

HRID 1493612 reaction equation
FC(F)(F)C(O)=O.[O-:8][C:9]#[N:10].[Na+].NN.[CH3:14][C:15]1[CH:16]=[C:17]([N:22]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[NH2:23])[CH:18]=[C:19]([CH3:21])[CH:20]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[NH2:10][C:9]([NH:23][N:22]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:17]1[CH:16]=[C:15]([CH3:14])[CH:20]=[C:19]([CH3:21])[CH:18]=1)=[O:8]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 54215552HCID 54215552, compound

Product 1

HCID 53693452HCID 53693452, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (1.06 ml, 13.9 mmol) was added under nitrogen to a stirred suspension of sodium cyanate (1.00 g, 15.2 mmol) in a solution of the hydrazine (Intermediate 36; 1.00 g, 4.8 mmol) in dry toluene (30 ml). The mixture was stirred for ca. 2 h, causing formation of a viscous insoluble gum. Saturated aqueous sodium hydrogen carbonate (25 ml) was added (causing effervescence and dissolution of the gum) and the mixture was extracted with ethyl acetate (3×75 ml). The combined extracts were washed with saturated brine (50 ml) dried and evaporated to afford a light yellow solid which was triturated with hexane/ethyl acetate (1:1) to give the title compound as a white powder (0.92 g, 76%), m.p. 139°-141°.

Workup

  1. dissolutioneffervescence and dissolution of the gum) and the mixture
  2. extractionwas extracted with ethyl acetate (3×75 ml)
  3. washThe combined extracts were washed with saturated brine (50 ml)
  4. customdried
  5. customevaporated
  6. customto afford a light yellow solid which
  7. customwas triturated with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-1c4ac296e03840ce85935610cad0b653
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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