Acetic Anhydride → HCID 58747570, compound

HRID 2378367Notes

Reaction equation

HRID 2378367 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[O:16][CH:15](NC)[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH:20]([N:23]([CH:26](C)C)CC)(C)[CH3:21].C(OC(=O)C)(=[O:31])C>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[O:16][CH:15]([CH2:26][NH:23][C:20](=[O:31])[CH3:21])[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86608753HCID 86608753, compound

Product 1

HCID 58747570HCID 58747570, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[7-(2-Chloro-phenyl)-2,3-dihydro-benzofuran-2-yl]-methylamine hydrochloride (0.050 g, 0.17 mmol) was suspended in 5.0 mL of methylene chloride and diisopropylethylamine (0.072 g, 0.56 mmol) and acetic anhydride (0.029 g, 0.28 mmol) added. The mixture was stirred at room temperature for 30 min, diluted to 100 mL with methylene chloride, washed with 50 mL portions of 2 N HCl (aqueous), saturated aqueous sodium bicarbonate and saturated brine. The solution was dried over sodium sulfate, filtered and concentrated in vacuum to give 0.047 g of the title compound as an oil which slowly hardened to a white solid in vacuum. 1H-NMR (CDCl3): doublet of doublets 7.48 δ (1H); multiplet 7.33 δ (2H); doublet 7.2 δ (1H); doublet 7.06 δ (1H); triplet 6.93 δ (1H); broad singlet 5.95 δ (1H); multiplet 4.9 δ (1H); doublet of doublets 3.7 δ (1H); doublet of doublets 3.45 δ (1H); doublet of doublets 3.35 δ (1H), doublet of doublets 3.0 δ (1H), singlet 1.95 δ (3H).

Workup

  1. washwashed with 50 mL portions of 2 N HCl (aqueous), saturated aqueous sodium bicarbonate and saturated brine
  2. dry with materialThe solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-4087f2f7875249c0a3f14c47c94de681
Source dataset
uspto-grants-2008_12
Patent number
US07470799B2

Reaction notes

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