Potassium Iodide → HCID 11516678, compound

HRID 2422574Notes

Reaction equation

HRID 2422574 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]([CH3:18])[C:16](=[O:19])[C:15]3[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>CN(C=O)C.C(OCC)(=O)C>[CH3:18][N:17]1[C:16](=[O:19])[C:15]2[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:22][CH2:23][CH2:24][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 80061-Bromo-3-chloropropaneHCID 8082PiperidineHCID 11430Potassium Carbonate2×HCID 136389335HCID 136389335, compound

Product 1

HCID 11516678HCID 11516678, compoundYield 8.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Hydroxyphenyl)-3,8-dimethyl-4(3H)-quinazolinone (500 mg, 1.88 mmol) was mixed with 1-chloro-3-bromopropane (326 mg, 2.07 mmol) and potassium carbonate (519 mg, 3.76 mmol) in DMF (5 ml), and stirred at 80° C. for 4 hours. After cooled to room temperature, potassium carbonate (519 mg, 3.76 mmol), potassium iodide (312 mg, 1.88 mmol) and piperidine (320 mg, 3.76 mmol) were added to the reaction solution, and further stirred at 80° C. for 12 hours. The reaction solution was diluted with ethyl acetate, then washed with aqueous 1 N sodium hydroxide solution and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (chloroform/methanol=5/1) and recrystallized from ethyl acetate to obtain the intended compound (63 mg, 8.6%) as a colorless solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. stirringfurther stirred at 80° C. for 12 hours
  3. washwashed with aqueous 1 N sodium hydroxide solution and saturated saline water in that order
  4. dry with materialthe organic layer was dried with magnesium sulfate
  5. customThe solvent was evaporated off
  6. customthe residue was purified through silica gel column chromatography (chloroform/methanol=5/1)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3ea608c094ea4c5e95bcc897e35d9141
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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