Trifluoroacetic acid → HCID 53659758, compound

HRID 1493611Notes

Reaction equation

HRID 1493611 reaction equation
NN.[CH2:3]([C:6]1[CH:7]=[C:8]([N:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[NH2:13])[CH:9]=[CH:10][CH:11]=1)[CH2:4][CH3:5].[O-:19][C:20]#[N:21].[Na+].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[NH2:21][C:20]([NH:13][N:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH2:3][CH2:4][CH3:5])[CH:7]=1)=[O:19]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 54249329Methyl [1-(3-propylphenyl)hydrazino]acetate

Product 1

HCID 53659758HCID 53659758, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The hydrazine (Intermediate 33; 910 mg, 4.1 mmol) was dissolved in dry toluene (30 ml) under nitrogen at room temperature. Sodium cyanate (880 mg, 13.5 mmol) was added to the reaction mixture, followed by trifluoroacetic acid (0.95 ml, 12.3 mmol). The reaction was stirred at room temperature for 3 h, then poured into sodium bicarbonate solution (30 ml, 8%) and extracted with ethyl acetate (3×75 ml). The combined dried (Na2SO4), organic phases were concentrated in vacuo to give a yellow oil. The crude material was triturated with ether and hexane to give the title compound (Intermediate 34; 500 mg, 46%) as a white powdery solid m.p. 111°-116°.

Workup

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. dry with materialThe combined dried (Na2SO4), organic phases
  3. concentrationwere concentrated in vacuo
  4. customto give a yellow oil
  5. customThe crude material was triturated with ether and hexane

Sources & evidence

ORD record
ord-eb34a55aaf6c459388c467e538309f1e
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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