Sodium sulfate decahydrate → HCID 178420359, compound

HRID 2288619Notes

Reaction equation

HRID 2288619 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[N:15]=[C:14]([C:16]2[S:17][C:18]([CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:19][CH:20]=2)[NH:13][N:12]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([NH:8][CH2:9][C:11]1[N:15]=[C:14]([C:16]2[S:17][C:18]([CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:19][CH:20]=2)[NH:13][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 18699992HCID 18699992, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 178420359HCID 178420359, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10 ml of anhydrous tetrahydrofuran solution containing 594 mg (1.5 mmol) of the compound obtained in Example 76 was added dropwise to 5 ml of anhydrous tetrahydrofuran suspension containing 230 mg (6.0 mmol) of lithium aluminum hydride, and the mixture was heated under reflux for 11 hours. Then, 460 mg (12.0 mmol) of lithium aluminum hydride was added and the mixture was again heated under reflux for 3 days. To the reaction mixture was added sodium sulfate decahydrate, the resulting insoluble matter was removed by filtration. The solvent was evaporated and then the resulting residue was purified by a silica gel column chromatography to give 104 mg of the title compound in its free form. By subjecting a 74 mg portion of this compound to salt formation using 33 mg of fumaric acid and recrystallizing it from methanol, 63 mg of the title compound was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 11 hours
  3. temperaturethe mixture was again heated
  4. temperatureunder reflux for 3 days
  5. customthe resulting insoluble matter was removed by filtration
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-e128f598fd034d89949a9ae023d53663
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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