Acetic Anhydride → HCID 58747567, compound

HRID 2378366Notes

Reaction equation

HRID 2378366 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[C:10]1[C:18]2[O:17][CH:16](NC)[CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1.[CH:21]([N:24]([CH:27](C)C)CC)(C)[CH3:22].C(OC(=O)C)(=[O:32])C>C(Cl)Cl>[Cl:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[C:4]=1[C:10]1[C:18]2[O:17][CH:16]([CH2:27][NH:24][C:21](=[O:32])[CH3:22])[CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86608751HCID 86608751, compound

Product 1

HCID 58747567HCID 58747567, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[7-(2,6-Dichloro-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 0.038 g of the title compound as a white crystalline solid.

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-49516bdfb6f645acb739328ef46cd4e0
Source dataset
uspto-grants-2008_12
Patent number
US07470799B2

Reaction notes

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