4-Aminobenzamide → 4-amino-N-(3,5-dimethylphenyl)benzamide

HRID 984551Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.I[C:12]1[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=1>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:8][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 760794-Aminobenzamide

HCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 85667044-amino-N-(3,5-dimethylphenyl)benzamideYield 98.4%

Procedure

Using general procedure A, 4-aminobenzamide (170 mg, 1.25 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 2:3; 15 mL fractions). Fractions 9-18 provided 246 mg (98% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.74-7.69 (m, 2H), 7.66 (br s, 1H), 7.28 (s, 2H), 6.78 (s, 1H), 6.74-6.69 (m, 2H), 4.05 (br s, 2H), 2.33 (s, 6H). 13C NMR (100 MHz, CDCl3): δ 165.7, 150.3, 139.1, 138.6, 129.2, 126.2, 124.8, 118.2, 114.6, 21.8.

Workup

customThe crude product was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 2:3; 15 mL fractions)

Sources & evidence

ORD record: ord-827db560b1c24386ada0af04f1bdc200
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867298B2

Reaction notes

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