Water → HCID 66976085, compound

HRID 1022748Notes

Reaction equation

HRID 1022748 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:6].[H-].[Na+].O>C1COCC1>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 4070176HCID 4070176, compound

Product 1

HCID 66976085HCID 66976085, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[(4-chlorobutanoyl)amino]benzoate (8.03 g) in THF (120 ml) was added 60% sodium hydride (2.14 g) at 0° C., and the mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into water, and the mixture was partitioned twice with ethyl acetate. The organic layers were combined, and the mixture was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.3 g).

Workup

  1. customthe mixture was partitioned twice with ethyl acetate
  2. washthe mixture was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3f2832b09df741a7ac297cbb0fc78710
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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