Dimethylformamide dimethyl acetal → HCID 68706092, compound

HRID 2232963Notes

Reaction equation

HRID 2232963 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:6]=[CH:14][N:15]([CH3:17])[CH3:16])=[O:5]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27359562,3-Dichlorobenzamide

Product 1

HCID 68706092HCID 68706092, compound

Procedure

2,3-Dichlorobenzamide (4.96 g, 26.1 mmol) and dimethylformamide dimethylacetal (10 mL) were heated at reflux for 1.5 hours, allowed to cool to room temperature, concentrated under reduced pressure, and the residue was partitioned between diethyl ether and water. The organic phase was washed with water (2×), saturated sodium chloride, dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate to provide the title compound. MS (DCI/NH3) m/z 245 (M+H)+.

Workup

  1. temperatureat reflux for 1.5 hours
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was partitioned between diethyl ether and water
  4. washThe organic phase was washed with water (2×), saturated sodium chloride
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5d7a81d5dcaa4807b9829a58aeaebb76
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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