Trifluoroacetic acid → 1-(3-Aminophenyl)imidazolidin-2-one

HRID 386470Notes

Reaction equation

HRID 386470 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][CH2:17][NH:16][C:15]2=[O:19])[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[CH:9]=[C:10]([N:14]2[CH2:18][CH2:17][NH:16][C:15]2=[O:19])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 65143068[3-(2-Oxo-imidazolidin-1-yl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 246884361-(3-Aminophenyl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [3-(2-oxo-imidazolidin-1-yl)-phenyl]-carbamic acid tert-butyl ester (0.88 g, 3.2 mmol) and trifluoroacetic acid (2 ml) in dichloromethane (10 ml) were stirred at room temperature for 5 hours. The reaction was quenched with sodium carbonate (20 ml) and extracted with dichloromethane (3×50 ml). The combined organics were dried (magnesium sulphate) and concentrated in vacuo (0.54 g, 96%). HPLC retention time 1 min. Mass spectrum (ES+) m/z 178 (M+H).

Workup

  1. customThe reaction was quenched with sodium carbonate (20 ml)
  2. extractionextracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organics were dried (magnesium sulphate)
  4. concentrationconcentrated in vacuo (0.54 g, 96%)

Sources & evidence

ORD record
ord-9e39599e83d44ca790f966879b66732c
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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