Hydrazine hydrate (1:1) → 1-Amino-3-(2,2,2-trifluoroethyl)imidazolidin-2-one

HRID 63833Notes

Reaction equation

HRID 63833 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:14][C:15]([F:18])([F:17])[F:16])[C:5](=O)[O:6]C1C=CC=CC=1.[NH2:19][NH2:20].O>C(O)C>[NH2:19][N:20]1[CH2:2][CH2:3][N:4]([CH2:14][C:15]([F:18])([F:17])[F:16])[C:5]1=[O:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118047012Phenyl N-(2-chloroethyl)-N-(2,2,2-trifluoroethyl)carbamate

Product 1

HCID 867756191-Amino-3-(2,2,2-trifluoroethyl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 250-mL round-bottom flask, was placed a solution of phenyl N-(2-chloroethyl)-N-(2,2,2-trifluoroethyl)carbamate (5.6 g, 19.88 mmol, 1.00 equiv) in ethanol (100 mL), NH2NH2.H2O (10 mL, 80%). The resulting solution was heated to reflux overnight in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate (1:1). This resulted in 0.8 g (22%) of 1-amino-3-(2,2,2-trifluoroethyl)imidazolidin-2-one as colorless oil. (ES, m/z): 184 [M+H]+

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux overnight in an oil bath
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThis resulted in 0.8 g (22%) of 1-amino-3-(2,2,2-trifluoroethyl)imidazolidin-2-one as colorless oil

Sources & evidence

ORD record
ord-bde14ba1044f4cf1886949c643ee5a50
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

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