1,2-Ethanediamine, N1-phenyl- → HCID 22648755, compound

HRID 393153Notes

Reaction equation

HRID 393153 reaction equation
Cl[CH:2]([C:6]1[C:7]([C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=[N:10][CH:11]=1)[CH:3]([CH3:5])[CH3:4].[C:16]1([NH:22][CH2:23][CH2:24][NH2:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(C)C>[CH3:4][CH:3]([CH3:5])[CH:2]([NH:25][CH2:24][CH2:23][NH:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]1[C:7]([C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 742701,2-Ethanediamine, N1-phenyl-HCID 22648742HCID 22648742, compound

Product 1

HCID 22648755HCID 22648755, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.05 g (4.2 mol) of 5-(1-chloro-2-methylpropyl)-4-trifluoromethylpyrimidine and 0.61 (4.2 mol) of N-phenylethylenediamine were added to 10 ml of isopropyl alcohol, followed by stirring at room temperature for 6 hours. After completion of the reaction, the reaction solution was concentrated, then poured into water and extracted with ethyl acetate, and purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate) to obtain 0.38 g of N-[2-methyl-1-(4-trifluoromethylpyrimidin-5-yl)-propyl]-N′-phenylethane-1,2-diamine. Then, 0.38 g (1 mmol) of N-[2-methyl-1-(4-trifluoromethylpyrimidin-5-yl)-propyl]-N′-phenylethane-1,2-diamine and 0.5 g (5 mmol) of triethylamine were added to 10 ml of dichloromethane, and a dichloromethane solution containing 0.2 g (2 mmol) of phosgene was dropwise added under cooling with ice. After the dropwise addition, stirring was further continued at room temperature for 1 hour to terminate the reaction. After termination of the reaction, the product was poured into water, washed with an aqueous sodium hydrogencarbonate solution, dried and concentrated, and the obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate) to obtain 0.25 g (yield: 61%) of 1-[2-methyl-1-(4-trifluoromethyl-pyrimidin-5-yl)-propyl]-3-phenylimidazolin-2-one as colorless crystals (melting point: 126-128° C.).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated
  3. additionpoured into water
  4. extractionextracted with ethyl acetate
  5. custompurified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-111bbb4e045747dda5d996ba7def7f37
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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