Acetone → HCID 15712398, compound

HRID 488693Notes

Reaction equation

HRID 488693 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([S:5][C:6]1[CH:15]=[CH:14][C:9](OC(=O)C)=[C:8]([OH:16])[C:7]=1[CH2:17][CH2:18][CH3:19])=[O:4].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][Br:28].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH3:37][C:38](C)=[O:39]>>[Br:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:16][C:8]1[C:7]([CH2:17][CH2:18][CH3:19])=[C:6]([S:5][C:3](=[O:4])[N:2]([CH3:1])[CH3:20])[CH:15]=[CH:14][C:9]=1[C:38](=[O:39])[CH3:37]

Participants

6

Reactant 5

HCID 180AcetoneHCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 123681,6-DibromohexaneHCID 86744526HCID 86744526, compound

Product 1

HCID 15712398HCID 15712398, compoundYield 79.7%

Procedure

A mixture of (4-(N,N-dimethylcarbamoylthio)-2-hydroxy-3 -propylphenoxy)ethanone (5.8 g), 1,6-dibromohexane (25 g), potassium iodide (1 g) and potassium carbonate (5.7 g) in acetone (40 ml) was heated with refluxing and stirring. Each of potassium carbonate (2.9 g) was added thereto after 9.5 hours, 20 hours and 30.5 hours, and the mixture was subjected to refluxing for total 41 hours. After cooled, inorganic materials were filtered off and the filtrate was concentrated under a reduced pressure. The resultant residue was purified through silica-gel column chromatography (eluting with benzene:hexane=1:1, then benzene:ethyl acetate=9: 1) to give (2-(6-bromohexyloxy)-4-(N,N-dimethylcarbamoylthio) -3-propylphenyl)ethanone (7.3 g, 79.7%) as brown oil. 1H-NMR (CDCl3) δ: 0.99 (3H, t, J=7 Hz, —CH2CH2CH3), 1.2-1.8 (10H, m, —CH2CH2CH3 and —OCH2CH2CH2CH2CH2CH2Br), 2.59 (3H, s, COCH3), 2.70 (2H, m, —CH2CH2CH3), 3.08 (6H, s, —N(CH3)2), 3.35 (2H, t, J=6 Hz, —CH2Br), 3.77 (2H, m, t, J=6 Hz, —OCH2(CH2)5Br), 7.30 (2H,

Workup

  1. temperaturewas heated
  2. temperaturewith refluxing
  3. custom20 hours and 30.5 hours
  4. temperatureto refluxing for total 41 hours
  5. temperatureAfter cooled
  6. filtrationinorganic materials were filtered off
  7. concentrationthe filtrate was concentrated under a reduced pressure
  8. customThe resultant residue was purified through silica-gel column chromatography (
  9. washeluting with benzene

Sources & evidence

ORD record
ord-78f505d42f154b30871977c9b7292da0
Source dataset
uspto-grants-2005_12
Patent number
USRE038921E1

Reaction notes

Loading…