Acetyl chloride → HCID 112757036, compound

HRID 588867Notes

Reaction equation

HRID 588867 reaction equation
[NH2:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CCN(CC)CC.[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([NH:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13498834HCID 13498834, compound

Product 1

HCID 112757036HCID 112757036, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 5-amino-2-chloro-4-methoxybenzoate (3.6 g, 16.7 mmol), Et3N (6.7 g, 66.8 mmol) and DCM (100 mL) at RT, acetyl chloride (1.57 g, 20.1 mmol) was added dropwise and the resulting mixture was stirred for 12 h. The reaction mixture was partitioned between dichloromethane and water. The organic layer was washed with saturated NaHCO3 solution and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1:1) to afford the desired product (2.7 g, 63% yield).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. washThe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1:1)

Sources & evidence

ORD record
ord-3fee4b9abee6400f9fae94e0631e9553
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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