Chloroacetaldehyde → HCID 70654370, compound

HRID 539465Notes

Reaction equation

HRID 539465 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[C:6](=[NH:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].Cl[CH2:20][CH:21]=O.C(=O)(O)[O-].[Na+]>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH3:14])[CH:20]=[CH:21][N:15]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 178490389HCID 178490389, compound

Product 1

HCID 70654370HCID 70654370, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 500 mL round bottom flask was added 3-methoxy-N-(o-tolyl)benzimidamide (6 g, 24.97 mmol), 2-chloroacetaldehyde (6.34 ml, 49.9 mmol), sodium bicarbonate (4.20 g, 49.9 mmol), and 100 mL 2-propanol. The reaction mixture was heated to reflux under nitrogen. The reaction mixture was concentrated, water was added, and the mixture was 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% ethyl acetate/hexane (5.58 g, 85%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added
  5. extractionthe mixture was 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% ethyl acetate/hexane (5.58 g, 85%)

Sources & evidence

ORD record
ord-3513f918f4e24df1875415d7314d3026
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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