Dichloromethane → HCID 69849532, compound

HRID 393154Notes

Reaction equation

HRID 393154 reaction equation
[CH3:1][CH:2]([CH3:24])[CH:3]([NH:14][CH2:15][CH2:16][NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4]1[C:5]([C:10]([F:13])([F:12])[F:11])=[N:6][CH:7]=[N:8][CH:9]=1.C(N(CC)CC)C.ClCCl.[C:35](Cl)(Cl)=[O:36]>O>[CH3:1][CH:2]([CH3:24])[CH:3]([N:14]1[CH2:15][CH2:16][N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:35]1=[O:36])[C:4]1[C:5]([C:10]([F:12])([F:11])[F:13])=[N:6][CH:7]=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 6371PhosgeneHCID 8471TriethylamineHCID 22648755HCID 22648755, compound

Product 1

HCID 69849532HCID 69849532, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. additionwas dropwise added
  2. temperatureunder cooling with ice
  3. additionAfter the dropwise addition
  4. customto terminate
  5. customthe reaction
  6. customAfter termination of the reaction
  7. washwashed with an aqueous sodium hydrogencarbonate solution
  8. customdried
  9. concentrationconcentrated
  10. customthe obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-0a71339639754f2bb4bf12f6cf184d9d
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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