Chlorosuccinimide → N-[3-(5-Chloro-7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

HRID 1602415Notes

Reaction equation

HRID 1602415 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[C:13]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:12][CH:11]=1>C(O)(=O)C>[Cl:1][C:12]1[CH:11]=[C:10]([F:9])[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[C:13]=1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 19611636N-[3-(7-Fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

Product 1

HCID 19611638N-[3-(5-Chloro-7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Chlorosuccinimide (47.7 mg) was added to a solution of N-[3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide (77 mg) in glacial acetic acid (5 ml) at room temperature under nitrogen and the mixture stirred for 72 h. The solution was evaporated and the residue partitioned between sodium carbonate (2N; 10 ml) and ethyl acetate (10 ml). The combined organic extracts were washed with brine (10 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by column chromatography. Eluting with dichloromethane/methanol 50:1 gave the title compound as a colourless gum which crystallised on standing (67 mg).

Workup

  1. customThe solution was evaporated
  2. customthe residue partitioned between sodium carbonate (2N; 10 ml) and ethyl acetate (10 ml)
  3. washThe combined organic extracts were washed with brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue purified by column chromatography
  7. washEluting with dichloromethane/methanol 50:1

Sources & evidence

ORD record
ord-5b817ceee4c1459498ef1a389eebb487
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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