Water → HCID 136099468, compound

HRID 899973Notes

Reaction equation

HRID 899973 reaction equation
[CH3:1][C:2]1([CH3:33])[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)[C:5](=[O:20])[N:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)[C:3]1=[O:32].Cl.N1C=CC=CC=1.O>C(Cl)Cl>[CH3:1][C:2]1([CH3:33])[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)[C:5](=[O:20])[N:4]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]([F:30])([F:31])[F:29])=[CH:25][CH:26]=2)[C:3]1=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 10176127Pyridinium chlorideHCID 59694201HCID 59694201, compound

Product 1

HCID 136099468HCID 136099468, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 0.89 g of 5,5-dimethyl-1-(7-methoxyquinolin-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione and 5.5 g of pyridine hydrochloride is heated at a temperature in the region of 220° C. for 4 hours. After cooling, 200 ml of water and 100 ml of CH2Cl2 are added. After separation of the phases by settling, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The solid obtained is purified by flash chromatography (SiO2, EtOAc/CH2Cl2 40/60 by volume as eluent, Ar). The fractions containing the product are concentrated under reduced pressure. 85 mg of 5,5-dimethyl-1-(7-hydroxyquinoline-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione are thus obtained, the characteristics of which product are as follows:

Workup

  1. temperatureAfter cooling
  2. customAfter separation of the phases
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe solid obtained
  7. customis purified by flash chromatography (SiO2, EtOAc/CH2Cl2 40/60 by volume as eluent, Ar)
  8. additionThe fractions containing the product
  9. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-615a73f39b1b428a8661d38b0cfc25fd
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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