Trifluoroacetic acid → 1-(2-aminoethyl)-2,3-dihydro-1H-imidazol-2-one; trifluoroacetic acid

HRID 561027Notes

Reaction equation

HRID 561027 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC(=O)[NH:14][CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][NH:19][C:18]1=[O:22])(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:14][CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][NH:19][C:18]1=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66997754[2-(2-Oxo-2,3-dihydro-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 717575481-(2-aminoethyl)-2,3-dihydro-1H-imidazol-2-one; trifluoroacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoro-acetic acid (10 mL) to a solution of [2-(2-oxo-2,3-dihydro-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (2.5 g, 11 mmol) in dichloromethane (10 mL). Stir the mixture for 3 hours. Remove most of the solvent and trifluoro-acetic acid on a rotovap and dry the yellowish thick oil under vacuum to get the product. GCMS (EI) m/z 127 M+.

Workup

  1. customRemove most of the solvent and trifluoro-acetic acid on a rotovap and
  2. customdry the yellowish thick oil under vacuum
  3. customto get the product

Sources & evidence

ORD record
ord-8d4f98290f09455cae340c6b470496d8
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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