Trifluoroacetic acid → HCID 54104674, compound

HRID 1493637Notes

Reaction equation

HRID 1493637 reaction equation
FC(F)(F)C(O)=O.NN.[CH3:10][O:11][C:12](=[O:31])[CH2:13][N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:17]=1)[NH2:15].[O-:32][C:33]#[N:34].[Na+]>C1(C)C=CC=CC=1>[NH2:34][C:33]([NH:15][N:14]([CH2:13][C:12]([O:11][CH3:10])=[O:31])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH:17]=1)=[O:32]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 517096Sodium CyanateHCID 131716907HCID 131716907, compound

Product 1

HCID 54104674HCID 54104674, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (2.75 ml, 35.8 mmol) was added at 25° to a stirred suspension of the hydrazine (Intermediate 79, 3.7 g, 12.2 mmol) and sodium cyanate (2.71 g, 41.75 mmol) in toluene (70 ml). The mixture was stirred at 25° for 1 h, during which time a white solid precipitated. 8% sodium bicarbonate (100 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were then washed with water (2×100 ml) and brine (100 ml) before drying (Na2SO4) and evaporating in vacuo to a yellow oil. Trituration with hexane/ether/ethyl acetate (1:1:4) gave the title compound (Intermediate 80) as a white crystalline solid (2.9 g; 68%) m.p. 119°-121°.

Workup

  1. customprecipitated
  2. addition8% sodium bicarbonate (100 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  4. washThe combined extracts were then washed with water (2×100 ml) and brine (100 ml)
  5. dry with materialbefore drying (Na2SO4)
  6. customevaporating in vacuo to a yellow oil

Sources & evidence

ORD record
ord-4857210121e84c5e8f586d78ea392584
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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