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

HRID 2115884Notes

Reaction equation

HRID 2115884 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]>C(Cl)Cl>[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

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 883681HCID 883681, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 DCM (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 RT and left to stir for 18 h. After 18 h the reaction had given a precipitate which was isolated by filtration and washed with DCM to give 2.28 g of a white solid, which was partitioned between DCM and a saturated aqueous NaHCO3 solution. The organic layer was removed under reduced pressure and the aqueous layer was then re-extracted DCM. 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.

Workup

  1. temperatureto warm to RT
  2. waitleft
  3. waitAfter 18 h the reaction had given
  4. customa precipitate which was isolated by filtration
  5. washwashed with DCM

Sources & evidence

ORD record
ord-73635815bfa34413a11930e323c8db3e
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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