Benzoyl chloride → HCID 18979261, compound

HRID 2393171Notes

Reaction equation

HRID 2393171 reaction equation
[NH2:1][CH:2]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[OH-].[Na+].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[C:24]([NH:1][CH:2]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 18979156HCID 18979156, compound

Product 1

HCID 18979261HCID 18979261, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

While a solution (5 ml) of ethyl 6-amino-6-(2-naphthyl)hexanoate in acetonitrile (1.0 g) and a 1N aqueous solution of sodium hydroxide (4 ml) were vigorously stirred together under ice-cooling, benzoyl chloride (0.54 g) was added dropwise and the mixture was further stirred at room temperature for 1 hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The extract and the organic layer were combined, dried, and concentrated to provide ethyl 6-benzoylamino-6-(2-naphthyl)hexanoate (1.5 g).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. extractionThe extract
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b25071dfd9a544bba87917fb42d983c2
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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