Hydrochloric Acid → HCID 66696264, compound

HRID 69104Notes

Reaction equation

HRID 69104 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21].Cl>O1CCCC1.O.C(OCC)(=O)C>[C:10]([C:3]1[CH:4]=[C:5]([Br:9])[C:6]([CH3:8])=[CH:7][C:2]=1[NH:1][C:20](=[O:22])[CH3:21])(=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 45098026HCID 45098026, compound

Product 1

HCID 66696264HCID 66696264, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 6.95 g of 1-(2-amino-5-bromo-4-methylphenyl)ethanone and 8.5 mL of triethylamine in 104 mL of tetrahydrofuran was slowly added 3.25 mL of acetyl chloride. After stirring at room temperature for 2 hours, the reaction mixture was poured into a mixture of water/ethyl acetate, followed by stirring for 30 minutes and adjusting to pH 3 with 6 M hydrochloric acid, and the aqueous layer was separated. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 6.33 g of N-(2-acetyl-4-bromo-5-methylphenyl)acetamide.

Workup

  1. stirringby stirring for 30 minutes
  2. customthe aqueous layer was separated
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e9a4d6d4e6e14d269ca9dc44d811b9a9
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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