Sodium Sulfate → HCID 19809062, compound

HRID 374071Notes

Reaction equation

HRID 374071 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([S:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][N:34]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:35](=O)[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=3[F:44])[NH:18][C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:11][CH:10]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:16]=[C:17]([S:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][N:34]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=3[F:44])[NH:18][C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 19021753HCID 19021753, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19809062HCID 19809062, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminium hydride (1N in tetrahydrofuran, 2 mL) in dry tetrahydrofuran (30 mL), a solution of N-[5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentyl]-2,4-difluoro-N-heptylbenzeneacetamide (0.70 g, 0.00107 mol) in dry tetrahydrofuran (15 mL) was added slowly. The reaction mixture was heated to reflux for 5 hours and was then allowed to cool to ambient temperature. The reaction mixture was poured into a mixture of 10% aqueous sodium sulfate (150 mL) and ice (150 mL). The resultant emulsion was filtered through Celite® and the filtrate was extracted with ethyl acetate (3×100 mL). The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo to give a crude oil. The product was purified by flash chromatography on silica gel (100 mL) eluting methanol: methylene chloride (5:95 v:v) to give the title compound as a viscous colorless oil (0.46 g, 0.000723 mol). 1H NMR (CDCl3) δ9.2-9.15(bs,1H), 7.56-7.25(m,4H), 7.11(m,1H), 6.94-6.70(m,6H), 3.81(m,6H), 3.07(t,2H), 2.74-2.58(m,4H), 2.43(m,4H), 1.71(m,2H), 1.53-1.20(m,14H), 0.91(t,3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationThe resultant emulsion was filtered through Celite®
  4. extractionthe filtrate was extracted with ethyl acetate (3×100 mL)
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a crude oil
  9. customThe product was purified by flash chromatography on silica gel (100 mL)
  10. washeluting methanol: methylene chloride (5:95 v:v)

Sources & evidence

ORD record
ord-10a815cba59e4c0cab622fe041675585
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

Loading…