Aluminium lithium hydride → HCID 43528715, compound

HRID 447877Notes

Reaction equation

HRID 447877 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[CH2:8][NH2:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66876873HCID 66876873, compound

Product 1

HCID 43528715HCID 43528715, compoundYield 142.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(Step 1) To a suspension of 2-[(2-methoxyethyl)sulfanyl]benzamide (12.0 g) in tetrahydrofuran (122 ml) was added lithium aluminum hydride (13.4 g) at 0° C. under a nitrogen atmosphere. The reaction mixture was heated under reflux for 5 hr, cooled to 0° C., and quenched successively with water (15 ml) and 15% aqueous sodium hydroxide solution (15 ml). The mixture was filtered through celite, and washed with dichloromethane. The filtrate was washed with saturated brine, and the organic layer was dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure to give 1-{2-[(2-methoxyethyl)sulfanyl]phenyl}methanamine (16.0 g) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 hr
  3. customquenched successively with water (15 ml) and 15% aqueous sodium hydroxide solution (15 ml)
  4. filtrationThe mixture was filtered through celite
  5. washwashed with dichloromethane
  6. washThe filtrate was washed with saturated brine
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d4ce4adc43fe405596aed9991a13ac06
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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