Hydrochloric Acid → HCID 58170479, compound

HRID 1619138Notes

Reaction equation

HRID 1619138 reaction equation
Cl.[I:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:6]#[N:7].[CH2:12]([OH:14])[CH3:13].C(OCC)C>C1C=CC=CC=1>[I:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:6](=[NH:7])[O:14][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 121296213-Iodo-4-methylbenzonitrile

Product 1

HCID 58170479HCID 58170479, compoundYield 189.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrogen chloride gas was bubbled over a period of 35 minutes into a stirred solution of 3-iodo-4-methylbenzonitrile (preparation 51a, 2.00 g, 8.2 mmol) and ethanol (0.70 mL, 12.3 mmol) in benzene at 0° C. The mixture was stirred for 30 minutes at room temperature and then the mixture was placed in the refrigerator and left overnight. Diethyl ether (200 mL) was then added and a white solid precipitated. After leaving the mixture a further night in the refrigerator the precipitate was filtered. Dichloromethane and saturated aqueous potassium carbonate solution were added to the solid with stirring. The organic layer was dried (MgSO4) and evaporated to give the title compound (4.50 g, 80%) as an oil.

Workup

  1. waitleft overnight
  2. customa white solid precipitated
  3. customAfter leaving the mixture a further night in the refrigerator the precipitate
  4. filtrationwas filtered
  5. additionDichloromethane and saturated aqueous potassium carbonate solution were added to the solid
  6. stirringwith stirring
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-5a2c58073106403dafeba4ab7eb29ad2
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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