Iodobenzene → 2-ethyl-N-phenylacetanilide

Reaction equation

[CH2:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2].I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:1]([CH2:3][C:4]([N:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 11575Iodobenzene

HCID 14323N-Phenylbutanamide

Product 1

HCID 126664572-ethyl-N-phenylacetanilideYield 56%

Procedure

Using 2-ethylacetanilide (4.9 g) and iodobenzene (12.4 ml), a reaction as made in the same manner as in 1) of Production Example 2. The subsequent purification by silica gel column chromatography (developing solvent, ethyl acetate:hexane=1:3) produced 2-ethyl-N-phenylacetanilide (4.0 g; yield, 56%) as a brown oil.

Workup

customa reaction
customThe subsequent purification by silica gel column chromatography (developing solvent, ethyl acetate:hexane=1:3)

Sources & evidence

ORD record: ord-57518f02591e4f799717cc480ff7fd23
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235730B1

Reaction notes

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