Potassium Hydroxide → HCID 15404433, compound

HRID 342905Notes

Reaction equation

HRID 342905 reaction equation
Br[C:2]1[S:3][C:4]([C:29]2[S:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=2)=[C:5]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]=1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[Na].[OH-:39].[K+]>O1CCOCC1>[CH2:8]([O:7][C:6]1[C:5]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:4]([C:29]2[S:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=2)[S:3][C:2]=1[C:2]1[S:3][C:4]([C:29]2[S:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=2)=[C:5]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]=1[O:39][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 5360545SodiumHCID 15404432HCID 15404432, compound

Product 1

HCID 15404433HCID 15404433, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-bromo-3,4-bis(decyloxy)-5-(benzothiazol-2-yl)-thiophene (12.2 g 20 mmol), and hexabutyl ditin (5.8 g, 10 mmol) in dioxane (100 ml), (freshly distilled from sodium after treatment with potassium hydroxide), was degassed by bubbling nitrogen through the solution for 20 min. Under nitrogen, tetrakistriphenylphosphinopalladium (0.468 g) was added and the mixture was heated at 100° C. for 20 hr. After cooling, pyridine (5 ml) was added and the resulting mixture allowed to stand for 1 hr. The separated solids were filtered and the filtrate diluted with an equal volume of water. The mixture was extracted with an equal volume of toluene, dried over magnesium sulfate and concentrated. The residue was combined with the initial solids and chromatographed over 250 g of silica gel. Elution with 3:1 and 2:1 heptane:toluene gave the desired product which was recrystallized from heptane to give 7.02 g (66.5% yield) mp 93.9°-95° C. Mass Spec. m/z 916 (M+ --C10H20). Elemental Analysis: Calculated for C62H92N2O4S4 : C, 70.36, H, 8.77, N, 2.65, and S, 12.10%. Found: C, 69.98, H, 8.90, N, 2.59, and S, 11.98 %.

Workup

  1. customwas degassed
  2. customby bubbling nitrogen through the solution for 20 min
  3. additionUnder nitrogen, tetrakistriphenylphosphinopalladium (0.468 g) was added
  4. temperatureAfter cooling
  5. additionpyridine (5 ml) was added
  6. filtrationThe separated solids were filtered
  7. additionthe filtrate diluted with an equal volume of water
  8. extractionThe mixture was extracted with an equal volume of toluene
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customchromatographed over 250 g of silica gel
  12. washElution with 3:1 and 2:1 heptane

Sources & evidence

ORD record
ord-40e3e127e5144d70bc12e02fa95da8b7
Source dataset
uspto-grants-1999_01
Patent number
US05859251

Reaction notes

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