Sodium Hydroxide → HCID 15982436, compound

HRID 493090Notes

Reaction equation

HRID 493090 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[S:11]1[CH:15]=[C:14]([S:16][C:17]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:18]=2[C:19]([NH:21][CH3:22])=O)[C:13]2[CH:28]=[CH:29][CH:30]=[CH:31][C:12]1=2.[OH-].[Na+]>C(OCC)C.C1COCC1.O>[S:11]1[CH:15]=[C:14]([S:16][C:17]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:18]=2[CH2:19][NH:21][CH3:22])[C:13]2[CH:28]=[CH:29][CH:30]=[CH:31][C:12]1=2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 68897026HCID 68897026, compound

Product 1

HCID 15982436HCID 15982436, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (250 g, 6.6 mmol) is suspended in dry diethyl ether (50 mL) and cooled to 0° C. Aluminum chloride (295 mg, 2.2 mmol) dissolved in dry diethyl ether (50 mL) is added dropwise at 0-5° C. The cooling bath is removed and the mixture is stirred at ambient temperature for 1 hour. The resulting aluminum hydride reagent solution is cooled to 0° C. followed by dropwise addition of of 2-(benzo[b]thiophen-3-ylsulfanyl)-5,N-dimethyl-benzamide (327 mg, 2.0 mmol) in 10 mL dry THF. After complete addition the solution is allowed to heat to ambient temperature and stirring is continued for 16 hours. The mixture is cooled to 10° C. followed by slow dropwise addition of water (0.5 mL) followed by 2M sodium hydroxide (0.5 mL) and water (2.5 mL) to quench excessive reducing agent. The mixture is filtered and concentrated in vacuo. The remanence is redissolved in ethyl acetate (100 mL), dried (MgSO4) and concentrated in vacuo. The product is purified by preparative HPLC or by silica gel chromatography eluting with ethyl acetate-triethyl amine to furnish the title compound.

Workup

  1. additionis added dropwise at 0-5° C
  2. customThe cooling bath is removed
  3. temperatureThe resulting aluminum hydride reagent solution is cooled to 0° C.
  4. additionAfter complete addition the solution
  5. temperatureto heat to ambient temperature
  6. stirringstirring
  7. waitis continued for 16 hours
  8. temperatureThe mixture is cooled to 10° C.
  9. customto quench excessive
  10. filtrationThe mixture is filtered
  11. concentrationconcentrated in vacuo
  12. dissolutionThe remanence is redissolved in ethyl acetate (100 mL)
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated in vacuo
  15. customThe product is purified by preparative HPLC or by silica gel chromatography
  16. washeluting with ethyl acetate-triethyl amine

Sources & evidence

ORD record
ord-9786f3a8cc7d4c06a1397d7354f24a7b
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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