Benzamide → HCID 21940658, compound

HRID 1242958Notes

Reaction equation

[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1I>>[CH3:10][N:11]([CH3:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 2331Benzamide

HCID 3013933Aniline, o-iodo-N,N-dimethyl-

Product 1

HCID 21940658HCID 21940658, compoundYield 95%

Procedure

Using general procedure A, benzamide (150 mg, 1.24 mmol) was coupled with N,N-dimethyl-2-iodoaniline (160 μL, 1.05 mmol). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 7:1; 15 mL fractions). Fractions 8–15 provided 239 mg (95% yield) of the product as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 9.42 (br s, 1H), 8.57 (dd, J=7.8, 1.4 Hz, 1H), 7.98–7.92 (m, 2H), 7.62–7.51 (m, 3H), 7.26 (dd, J=7.8, 1.4 Hz, 1H), 7.22 (td, J=7.8, 1.4 Hz, 1H), 7.12 (td, J=7.8, 1.4 Hz, 1H), 2.74 (s, 6H).

Workup

customThe crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 7:1; 15 mL fractions)

Sources & evidence

ORD record: ord-c99d87542c6146b48702b177882309ca
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115784B2

Reaction notes

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