Chloroacetyl chloride → HCID 57869938, compound

HRID 1045661Notes

Reaction equation

HRID 1045661 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.[NH2:7][CH:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10][CH2:9]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][CH2:2][C:3]([NH:7][CH:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10][CH2:9]1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2055871714105-88-5

Product 1

HCID 57869938HCID 57869938, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chloroacetyl chloride (41.6 g, 368 mmol) was added to a solution of 3-amino-chroman-4-one hydrochloride (67 g, 335 mmol) and triethylamine (102 g, 1.01 mol) in tetrahydrofuran (700 ml) and the mixture was stirred for one hour. The solution was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-(4-oxo-chroman-3-yl)-acetamide (22.6 g, 94.3 mmol, 28%) as white crystals.

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

Sources & evidence

ORD record
ord-e6c7353401eb46f9a8ff1e7de3bd001f
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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