2,2,2-Trifluoroethylhydrazine → HCID 178516751, compound

HRID 1452456Notes

Reaction equation

HRID 1452456 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([C:14](=[NH:18])OCC)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N[CH2:38][C:39](O)=[O:40])C1C=CC=CC=1.[F:42][C:43]([F:48])([F:47])[CH2:44][NH:45][NH2:46]>C(Cl)Cl.C(O)C>[CH2:1]([C:8]1[CH:9]=[C:10]([C:14]2[NH:18][CH2:38][C:39](=[O:40])[N:45]([CH2:44][C:43]([F:48])([F:47])[F:42])[N:46]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 787402,2,2-TrifluoroethylhydrazineHCID 68950700HCID 68950700, compoundHCID 87633496HCID 87633496, compound

Product 1

HCID 178516751HCID 178516751, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of ethyl 3-benzylbenzenecarboximidoate (0.5 g, 1.8 mmol) in methylene chloride (100 mL) was washed with saturated aqueous sodium bicarbonate (2×80 mL) brine (50 mL), dried over magnesium sulfate and concentrated to 6 mL. To this was added benzylglycinate p-toluenesulfonate (0.615 g, 1.8 mmol) in portions over 10 minutes, stirred at room temperature under nitrogen for 14 hours, and concentrated under reduced pressure to leave a pink gum which was dissolved in absolute ethanol (6 mL). Following dropwise addition of a solution of 1,1,1-trifluoroethylhydrazine in ethanol (70 percent, 0.19 mL, 1.8 mmol), the reaction mixture was stirred at room temperature under nitrogen for 14 hours, adsorbed onto silica and chromatographed on silica, eluting with a ethyl acetate/hexane mobile phase. The major fraction was concentrated under reduced pressure to leave a fluffy, yellowish solid. Yield 0.345 g (63 percent). mp 104-106° C.; 1H NMR (CDCl3) δ 7.50-7.46 (m, 2H), 7.37-7.16(m, 7H), 4.9 (br, 1H), 4.40 (q, J=8.7 Hz, 2H), 4.12 (s, 2H), 4.02 (s, 2H); ES/MS 347 m/e (M+).

Workup

  1. washwas washed with saturated aqueous sodium bicarbonate (2×80 mL) brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to 6 mL
  4. concentrationconcentrated under reduced pressure
  5. customto leave a pink gum which
  6. stirringthe reaction mixture was stirred at room temperature under nitrogen for 14 hours
  7. customchromatographed on silica
  8. washeluting with a ethyl acetate/hexane mobile phase
  9. concentrationThe major fraction was concentrated under reduced pressure
  10. customto leave a fluffy, yellowish solid

Sources & evidence

ORD record
ord-dd86aa92f7054672ba49cb180d5c8b5d
Source dataset
uspto-grants-2009_01
Patent number
US07473669B2

Reaction notes

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