Dimethylformamide dimethyl acetal → HCID 178425868, compound

HRID 1619133Notes

Reaction equation

HRID 1619133 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH2:7])=[O:6].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[CH3:14][N:15](/[CH:17]=[N:7]/[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=1)[CH3:16]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 8333293-iodo-4-methylbenzamide

Product 1

HCID 178425868HCID 178425868, compoundYield 78.1%

Conditions

Temperature
90 °C

Procedure

A suspension of 3-iodo-4-methylbenzamide (preparation 48a, 2.00 g, 7.7 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (4.0 mL, 30.1 mmol) was heated in a sealed tube at 90° C. with stirring. After 2 hours, the mixture was cooled and concentrated in vacuo. The residue was triturated with diethyl ether and hexanes, and the solid that formed was filtered and dried to give the title compound (1.90 g, 78%) as a yellow solid.

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with diethyl ether and hexanes
  4. customthe solid that formed
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-a96c8de0f841459bbe2e42d048a83120
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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