Chloroacetaldehyde → HCID 70654448, compound

HRID 539467Notes

Reaction equation

HRID 539467 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5](=[NH:14])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].Cl[CH2:19][CH:20]=O.C(=O)(O)[O-].[Na+]>CC(O)C>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:13])[CH:19]=[CH:20][N:14]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 178424365HCID 178424365, compound

Product 1

HCID 70654448HCID 70654448, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 500 mL round bottom flask was added 3-iodo-N-(o-tolyl)benzimidamide (7.77 g, 23.11 mmol), 2-chloroacetaldehyde (5.87 ml, 46.2 mmol), sodium bicarbonate (3.88 g, 46.2 mmol), and 100 mL 2-propanol. The reaction mixture was heated to reflux under nitrogen for 5 hours. The reaction mixture was concentrated, water was added, and the mixture extracted three times with ethyl acetate. The organic extracts were dried over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography eluting with 40 and 50% ethyl acetate/hexane (4.6 g, 55%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen for 5 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added
  5. extractionthe mixture extracted three times with ethyl acetate
  6. dry with materialThe organic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography
  10. washeluting with 40 and 50% ethyl acetate/hexane (4.6 g, 55%)

Sources & evidence

ORD record
ord-60749e5a51054adb86faf9f8b6b5eb62
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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