Trifluoroacetic acid → HCID 19829876, compound

HRID 1493632Notes

Reaction equation

HRID 1493632 reaction equation
FC(F)(F)C(O)=O.NN.[CH2:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([N:23]([CH2:25][C:26]([O:28]C)=O)[NH2:24])[CH:20]=[CH:21][CH:22]=1)[CH3:11].[O-:30][C:31]#[N:32].[Na+]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:25][C:26](=[O:28])[NH:32][C:31](=[O:30])[NH:24]2)[CH:20]=[CH:21][CH:22]=1)[CH3:11]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 517096Sodium CyanateHCID 54244762HCID 54244762, compound

Product 1

HCID 19829876HCID 19829876, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (7.32 ml, 95 mmol) was added dropwise to a suspension of the hydrazine (Intermediate 73, 8.94 g, 31.7 mmol) and sodium cyanate (7.21 g, 11 mmol) in toluene (63 ml) at room temperature. After stirring for 30 min the mixture was taken up in chloroform, quenched (NaHCO3), extracted (CHCl3), washed (H2O, sat. NaCl), dried (Na2SO4) and concentrated. The residue was subjected to column chromatography (SiO2, 10% MeOH in CHCl3) to afford the title compound as a pale yellow glass (6.78 g, 66%).

Workup

  1. customquenched (NaHCO3)
  2. extractionextracted (CHCl3)
  3. washwashed (H2O, sat. NaCl)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e2abaf9132444e3891c79a269b4da938
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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