Trifluoroacetic acid → HCID 53949497, compound

HRID 1493616Notes

Reaction equation

HRID 1493616 reaction equation
NN.[CH3:3][O:4][C:5](=[O:17])[CH2:6][N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[CH:10]=1)[NH2:8].[O-:18][C:19]#[N:20].[Na+].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.CCOCC>[NH2:20][C:19]([NH:8][N:7]([CH2:6][C:5]([O:4][CH3:3])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[CH:10]=1)=[O:18]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 517096Sodium CyanateHCID 19829962HCID 19829962, compound

Product 1

HCID 53949497HCID 53949497, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To the hydrazine (Intermediate 39; 3.75 g; 0.018 mol) and sodium cyanate (3.54 g; 0.054 mol) in toluene (30 ml) was added, dropwise, trifluoroacetic acid (5.82 g; 3.93 ml; 0.051 mol). This mixture was stirred for 3 h. and was then quenched with sodium bicarbonate and extracted into ethyl acetate. The organic extract was washed with sodium bicarbonate, water and brine and then dried (Na2SO4). Filtration and evaporation gave a cream solid which, on trituration with ether, afforded the title compound as a white solid (2.21 g; 49%), m.p. 128°-130° C.

Workup

  1. customwas then quenched with sodium bicarbonate
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with sodium bicarbonate, water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and evaporation
  7. customgave a cream solid which

Sources & evidence

ORD record
ord-195d65dd3b6b4bad93ee292a98e4cc80
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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