Dimethylformamide → HCID 86664265, compound

HRID 2387721Notes

Reaction equation

HRID 2387721 reaction equation
[H-].[Na+].[CH2:3]1C[O:6][CH2:5][CH2:4]1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-:16].[NH4+:17].[CH3:18][N:19]([CH:21]=O)C>C(OCC)C>[CH2:8]([O:6][C:5]1[C:4]([CH3:3])=[N:17][C:21]([Cl:16])=[N:19][CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 86664265HCID 86664265, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride (60% oil dispersion; 66.2 mg) was added to a THF solution (4.0 ml) of the compound Prep 1-2 (200 mg), and the obtained mixture was then stirred at room temperature for 10 minutes. Thereafter, benzyl bromide (197 ul) was added to the reaction solution. The obtained mixture was stirred at room temperature for 2 hours. Thereafter, DMF (2.0 ml) was added to the reaction solution, and the obtained mixture was then stirred for 4 hours. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction mixture, and liquid separation and extraction were carried out with diethyl ether. The obtained organic layer was dried over magnesium sulfate, and the solvent was then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate), so as to obtain the title compound (317 mg).

Workup

  1. stirringThe obtained mixture was stirred at room temperature for 2 hours
  2. stirringthe obtained mixture was then stirred for 4 hours
  3. dry with materialThe obtained organic layer was dried over magnesium sulfate
  4. concentrationthe solvent was then concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate)

Sources & evidence

ORD record
ord-5433be813dfd4ff9b04314135c940fa2
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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