HCID 12445986, compound → HCID 11429912, compound

HRID 902964Notes

Reaction equation

HRID 902964 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:13]=3[S:12](=O)(=O)[C:11]=2[CH:29]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:30]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:13]=3[S:12][C:11]=2[CH:29]=1)[CH3:31]

Participants

4

Reactant 2

HCID 12445986HCID 12445986, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11429912HCID 11429912, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. mixture of 3,7-bis(2-diethylaminoethoxy)dibenzothiophene-5,5-dioxide (5.30 g, 1.2 mmol; see J. Med. Chem., 1978, 21, 1084) in dry THF (10 mL) was added portion-wise lithium aluminum hydride (90 mg, 2.4 mmol, Aldrich). The reaction mixture was allowed to warm to ambient temperature and then heated at reflux for 2 hours. After cooling to room temperature, the reaction mixture was quenched by sequential addition of H2O-THF (1:9, 1 mL), aq. NaOH (2.5 N, 0.1 mL), and H2O (0.3 mL). The mixture was stirred for 30 minutes, filtered, and the residue was purified by flash chromatography (35 g silica gel, eluting with 4-8% of 10% NH4OH/MeOH in CH2Cl2) to afford the title compound (250 mg, 51% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling to room temperature
  4. customthe reaction mixture was quenched by sequential addition of H2O-THF (1:9, 1 mL), aq. NaOH (2.5 N, 0.1 mL), and H2O (0.3 mL)
  5. filtrationfiltered
  6. customthe residue was purified by flash chromatography (35 g silica gel, eluting with 4-8% of 10% NH4OH/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ddcf634280e9470f9b5a298d3acbd98b
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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