Acetone → HCID 15712398, compound

HRID 704120Notes

Reaction equation

HRID 704120 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), 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, t, J=6 Hz, --OCH2 (CH2)5Br), 7.30 (2H, ##STR23## ).

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-e198a5314c1441038674c3899715f525
Source dataset
uspto-grants-1991_01
Patent number
US04985585

Reaction notes

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