Potassium Hydroxide → HCID 18319270, compound

HRID 1701005Notes

Reaction equation

HRID 1701005 reaction equation
[OH-:1].[K+].[C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[CH3:18])[CH:8]=[CH:9][CH:10]=1)#[N:4]>C(O)C.O>[C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[CH3:18])[CH:8]=[CH:9][CH:10]=1)(=[O:1])[NH2:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18319289HCID 18319289, compound

Product 1

HCID 18319270HCID 18319270, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (1.21 gm, 21.6 mmol) was added to a solution of 1-(3-cyanophenyl)-4-iodo-2-methylbenzene (1.27 gm, 4.0 mmol) in ethanol (50 mL) and heated under reflux for 16 h. After being cooled, the mixture was diluted with water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to give crude product (1.08 gm). The crude product (540 mg) was purified by flash chromatography (gradient elution with dichloromethane:sat. methanolic ammonia 100:2.5 to dichloromethane:ethyl acetate 1:1 to dichloromethane:ethyl acetate:acetic acid 100:100:4), then azeotroped with ethanol, ethyl acetate and diethyl ether to give 1-(3-carbamoylphenyl)-4-iodo-2-methylbenzene (310 mg, 46%) as a buff solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter being cooled
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customto give crude product (1.08 gm)
  8. customThe crude product (540 mg) was purified by flash chromatography (gradient elution with dichloromethane:sat. methanolic ammonia 100:2.5 to dichloromethane:ethyl acetate 1:1 to dichloromethane:ethyl acetate:acetic acid 100:100:4)
  9. customazeotroped with ethanol, ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-5ad36598a45043ddb58c5b222cc8a7b1
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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