Benzoyl chloride, 3-nitro- → HCID 883681, compound

HRID 2117630Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH2:17]>ClCCl>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH:17][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Nitrobenzoyl chloride (2 g, 10.77 mmol) was loaded into a round bottomed flask, placed under a N2 atmosphere and dissolved in anhydrous dichloromethane (10 mL). The mixture was cooled to 0° C. and N,N-dimethylethylenediamine (0.98 mL, 8.98 mmol) was added to the reaction. The reaction was allowed to warm to room temperature and left to stir for 18 h. After 18 h the reaction had given a precipitate which was isolated by filtration and washed with dichloromethane to give 2.28 g of a white solid, which was partitioned between dichloromethane and a saturated aqueous NaHCO3 solution. The organic layer was removed under educed pressure and the aqueous layer was then re-extracted dichloromethane. The organic layers were combined, dried over Na2SO4 and the solvent was removed under reduced pressure to afford the title compound as a yellow solid. MS: 193, 238; 1H NMR (400 MHz, dmso-d6): 2.19 (6H, s), 2.42 (2H, t, J 6.8 Hz), 3.39 (2H, q, J 12.4 Hz, 6.7 Hz), 7.78 (1H, t, J 7.9 Hz), 8.29 (1H, ddd, J 7.9 1.8, 1.1 Hz), 8.38 (1H, ddd, J 8.1 Hz, 2.3, 1.0 Hz), 8.68 (1H, t, J 1.8 Hz), 8.81 (1H, t, J 5.7 Hz).

Workup

temperatureto warm to room temperature
waitleft
waitAfter 18 h the reaction had given
customa precipitate which was isolated by filtration
washwashed with dichloromethane

Sources & evidence

ORD record: ord-b2e8ce91f098454a9729a000054feb8f
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442698B2

Reaction notes

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