Acetanilide → N-[4-(N-acetyl-N-phenylamino)butyl]phthalimide

HRID 54916

Reaction equation

[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:5])[CH3:4].Br[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].O>CN(C)C=O>[C:3]([N:6]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Oily sodium hydride (60%, 2.45 g) was added to a solution of acetanilide (7.0 g) in N,N-diemthylformamide (50 ml), and the mixture was stirred at 0° C. for 15 minutes. Then a solution of N-(4-bromobutyl)phthalimide (15.3 g) in N,N-dimethylformamide (80 ml) was added dropwise. The mixture was stirred at room temperature for 4 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), and then the solvent was distilled off. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate-chloroform (1:9, v/v) to obtain N-[4-(N-acetyl-N-phenylamino)butyl]phthalimide (9.21 g, 52.9%), which was then recrystallized from isopropyl ether. Colorless prism, mp: 83°-84° C.

Workup

stirringThe mixture was stirred at room temperature for 4 hours
extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried (MgSO4)
distillationthe solvent was distilled off
washeluted with ethyl acetate-chloroform (1:9, v/v)

Sources & evidence

ORD record: ord-cb4444d5b1494200a98af26a206ff623
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624917

Linked notes

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