Diethylenetriamine → 2,2,2-trifluoro-N-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide

HRID 1434488Notes

Reaction equation

HRID 1434488 reaction equation
C(O[C:4](=[O:9])[C:5]([F:8])([F:7])[F:6])C.[NH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][NH2:16]>C1COCC1>[NH:13]([CH2:14][CH2:15][NH:16][C:4](=[O:9])[C:5]([F:6])([F:7])[F:8])[CH2:12][CH2:11][NH:10][C:4](=[O:9])[C:5]([F:8])([F:7])[F:6]

Participants

4

Reactant 2

HCID 8111DiethylenetriamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 3887782,2,2-trifluoro-N-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamideYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic acid ethyl ester (50 g; 0.35 mol) was dropped into a solution of diethylenetriamine (18 g; 0.175 mol) in THF (180 mL) at 0° C. in 1 h. After 20 h at room temperature, the mixture was evaporated to an oily residue (54 g). The oil was crystallized from Et2O (50 mL), filtered, washed with cooled Et2O (2×30 mL) and dried to obtain A as a white solid (46 g; 0.156 mol). Yield 89%.

Workup

  1. customthe mixture was evaporated to an oily residue (54 g)
  2. customThe oil was crystallized from Et2O (50 mL)
  3. filtrationfiltered
  4. washwashed with cooled Et2O (2×30 mL)
  5. customdried
  6. customto obtain A as a white solid (46 g; 0.156 mol)

Sources & evidence

ORD record
ord-82fdca9d33cf4f10a29cc2d19df507e7
Source dataset
uspto-grants-2009_11
Patent number
US07611692B2

Reaction notes

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