Dimethylformamide → HCID 68704565, compound

HRID 2234184Notes

Reaction equation

HRID 2234184 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:4][CH:3]=1.[C:16](Cl)(=[O:20])[C:17](Cl)=O.[CH3:22][N:23]([CH3:26])C=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([N:23]([CH2:22][CH:9]([O:20][CH2:16][CH3:17])[O:10][CH2:11][CH3:12])[CH2:26][CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 687011183-(4-Bromophenethoxy)propanoic acid

Product 1

HCID 68704565HCID 68704565, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[2-(4-Bromophenyl)ethoxy]propanoic acid (Example 10b), 0.46 g) was dissolved in dichloromethane (10 mL) and treated with oxalyl chloride (0.28 g) and a drop of dimethylformamide. The resultant solution was stirred at room temperature for 1.5 hours. The solution was then concentrated and azeotroped with dichloromethane (2×10 mL). The residue was dissolved in dichloromethane (10 mL) and added, portionwise, to a stirred solution of 2,2-diethoxy-N-phenethyl-ethanamine (0.40 g) and diisopropylamine (0.5 mL), dissolved in dichloromethane (5 mL). The resultant solution was stirred for 2 hours, concentrated and taken up in ethyl acetate (30 mL). Washing with water (2×30 mL), and brine (30 mL) followed by drying over anhydrous magnesium sulphate, filtering and concentration gave the sub-titled compound (0.72 g) as an oil.

Workup

  1. concentrationThe solution was then concentrated
  2. customazeotroped with dichloromethane (2×10 mL)
  3. dissolutionThe residue was dissolved in dichloromethane (10 mL)
  4. additionadded
  5. dissolutionportionwise, to a stirred solution of 2,2-diethoxy-N-phenethyl-ethanamine (0.40 g) and diisopropylamine (0.5 mL), dissolved in dichloromethane (5 mL)
  6. concentrationconcentrated
  7. washWashing with water (2×30 mL), and brine (30 mL)
  8. dry with materialby drying over anhydrous magnesium sulphate
  9. filtrationfiltering
  10. concentrationconcentration

Sources & evidence

ORD record
ord-e8052587329f4a4cbdd156a284d38882
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

Loading…