Sodium Sulfate → HCID 69058379, compound

HRID 2202839Notes

Reaction equation

HRID 2202839 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10](=O)[NH:11][C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[C:14]([CH3:19])[C:13]=1[NH2:20])C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br:18][C:16]1[CH:17]=[C:12]([NH:11][CH3:10])[C:13]([NH2:20])=[C:14]([CH3:19])[CH:15]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86635792HCID 86635792, compound

Product 1

HCID 69058379HCID 69058379, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of lithium aluminum hydride (400 mg) in THF (25 ml) was added a solution of ethyl(2-amino-5-bromo-3-methylphenyl)carbamate (1 g) in THF (10 ml) at 0° C. The mixture was then warmed to room temperature, followed by heating at reflux for 1 h. The reaction mixture was cooled to 0° C., diluted with THF (45 ml) and a saturated Na2SO4 solution was added dropwise thereto. The mixture was further stirred for 30 min and solids were filtered over Celite. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (550 mg) as a brownish liquid.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. filtrationsolids were filtered over Celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-a2f615fbf76447cea15cecd4fbdea3a6
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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