Sodium Carbonate → HCID 19611673, compound

HRID 1602413Notes

Reaction equation

HRID 1602413 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH2:16][CH2:15][C:14]=2[C:18]=1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Cl:9][C:10]1[CH:11]=[C:12]([Cl:1])[C:13]2[O:17][CH2:16][CH2:15][C:14]=2[C:18]=1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31398ChlorosuccinimideHCID 19611689HCID 19611689, compound

Product 1

HCID 19611673HCID 19611673, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Chlorosuccinimide (173 mg) was added to a solution of N-[3-(5-chloro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide (0.2 g) in glacial acetic acid (5 ml) at room temperature under nitrogen and the mixture stirred for 64 h. The solution was adusted to pH 9 with sodium carbonate (2N; 10 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with brine (20 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by HPLC, eluting with 50% acetonitrile/water+0.1% TFA gave the title compound as a colourless gum (97 mg)

Workup

  1. extractionextracted with ethyl acetate (3×15 ml)
  2. washThe combined organic extracts were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe residue purified by HPLC
  6. washeluting with 50% acetonitrile/water+0.1% TFA

Sources & evidence

ORD record
ord-e64b8db4ffac4f86b25631b334f85a7d
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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