Dimethylformamide dimethyl acetal → N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide

HRID 69105Notes

Reaction equation

HRID 69105 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[C:7]([CH3:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14])(=[O:3])[CH3:2].CO[CH:18]([N:21]([CH3:23])[CH3:22])OC>C1(C)C=CC=CC=1>[Br:10][C:8]1[C:7]([CH3:11])=[CH:6][C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([C:1](=[O:3])/[CH:2]=[CH:18]/[N:21]([CH3:23])[CH3:22])[CH:9]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 66696264HCID 66696264, compound

Product 1

HCID 86694309N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamideYield 90.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Under a nitrogen atmosphere, 6.33 g of N-(2-acetyl-4-bromo-5-methylphenyl)acetamide was added to a mixture of 3.3 g of (dimethoxymethyl)dimethylamine and 19 mL of toluene, followed by stirring at 120° C. for 16 hours. The mixture was cooled to room temperature, concentrated, and diisopropyl ether was added thereto and triturated. The powder was collected by filtration, washed with diisopropyl ether, and then dried under reduced pressure to obtain 6.92 g of N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiisopropyl ether was added
  4. customtriturated
  5. filtrationThe powder was collected by filtration
  6. washwashed with diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-77f0d155120141cb9eba0c64f04a4e7c
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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