Acetyl chloride → N-(2-((3S)-6-((2,4-Dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)acetamide

HRID 591528Notes

Reaction equation

HRID 591528 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14][NH2:15])[CH2:11][O:12][C:8]=2[CH:7]=1.[C:23](Cl)(=[O:25])[CH3:24].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14][NH:15][C:23](=[O:25])[CH3:24])[CH2:11][O:12][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 897679342-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanamine

Product 1

HCID 89767912N-(2-((3S)-6-((2,4-Dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)acetamideYield 47.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanamine (320 mg) and DMA (10 mL) was added acetyl chloride (74.3 mg). The mixture was stirred for 2 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (170 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-6da8f0cba98f4deeb296a3bf9e1dc3fc
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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