Potassium Iodide → HCID 19980025, compound

HRID 1461204Notes

Reaction equation

HRID 1461204 reaction equation
[CH2:1]([O:5][C:6](=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Br)[CH2:2][CH2:3][CH3:4].[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC>[CH3:14][N:15]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 544772HCID 544772, compound

Product 1

HCID 19980025HCID 19980025, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 111 g (0.44 mol) of butyl-6-bromohexanoate (Example 21), 50 g (0.46 mol) of N-methylaniline, 63.9 g (0.46 mol) of anhydrous potassium carbonate, 3.6 g (0.022 mol) of potassium iodide, and 500 mL of butanol was heated at reflux with stirring for 60 hours. The resulting suspension was cooled and filtered, and the solid was extracted with ethyl acetate. The extract was combined with the filtrate and the solvents were removed by rotary evaporation. The residue was distilled in vacuo, bp 183°-188° C. (0.1 mm). A slightly yellow oil was obtained, mass 60 g (50%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureThe resulting suspension was cooled
  4. filtrationfiltered
  5. extractionthe solid was extracted with ethyl acetate
  6. customthe solvents were removed by rotary evaporation
  7. distillationThe residue was distilled in vacuo, bp 183°-188° C. (0.1 mm)
  8. customA slightly yellow oil was obtained

Sources & evidence

ORD record
ord-1d51e7862db044d1b2d2e65bdb9ef149
Source dataset
uspto-grants-1991_12
Patent number
US05075043

Reaction notes

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