Sodium Chloride → HCID 19382363, compound

HRID 2400044Notes

Reaction equation

HRID 2400044 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[Br:22][CH2:23][C:24](Br)=[O:25].[Na+].[Cl-]>C(Cl)Cl.C(OCC)(=O)C>[Br:22][CH2:23][C:24]([NH:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:25]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8471Triethylamine2×HCID 61147Bromoacetyl bromide2×HCID 19382365HCID 19382365, compound

Product 1

HCID 19382363HCID 19382363, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Amino-2-benzoylfuran (4.93 g, 0.025 mol) was dissolved in s dry methylene chloride (50 mL). The solution was cooled to 0° C. under nitrogen and triethylamine (3.8 mL, 0.0275 mol) was added followed by bromoacetyl bromide (2.4 mL, 0.0275 mol). The mixture was stirred at 0° C. for five hours. Next another 10% of triethylamine and bromoacetyl bromide were added and the reaction was left over night. Ehtyl acetate (200 mL) and saturated NaCl (75 mL) were added. The ethyl acetate layer was separated, washed with saturated NaCl solution, dried over sodium sulfate, filtered and concentrated in vacuo. A tan solid was obtained in theoretical yield (7.7 g).

Workup

  1. waitthe reaction was left over night
  2. customThe ethyl acetate layer was separated
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customA tan solid was obtained
  8. customin theoretical yield (7.7 g)

Sources & evidence

ORD record
ord-c6b4b92157d04dbb8f7bc3e27e3de034
Source dataset
uspto-grants-1995_09
Patent number
US05453424

Reaction notes

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