Dimethylamine → 3-Fluoro-N,N-dimethyl-4-nitrobenzamide

HRID 2217592Notes

Reaction equation

HRID 2217592 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](Cl)=[O:6].[CH2:14]([N:16](CC)[CH2:17]C)C.CNC.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([N:16]([CH3:17])[CH3:14])=[O:6]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 8471TriethylamineHCID 27746563-Fluoro-4-nitrobenzoyl chloride

Product 1

HCID 221815783-Fluoro-N,N-dimethyl-4-nitrobenzamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 3 (1.50 g, 7.36 mmol) in CH2Cl2 (30 mL) at 0° C. was added triethylamine (1.5 mL, 10.9 mmol) and dimethylamine 40% in water (0.83 mL, 7.36 mmol) dropwise. The solution was stirred and allowed to warm to RT overnight before concentrating under reduced pressure and adding EtOAc. The solution was washed sequentially with saturated NaHCO3, water, and brine, before drying over MgSO4 and concentrating under reduced pressure to give impure 4 (0.78 g, 50%). MS: APCI (AP+): 213.1 (M)+, (AP−): 212.1 (M)−.

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. additionadding EtOAc
  3. washThe solution was washed sequentially with saturated NaHCO3, water, and brine
  4. dry with materialbefore drying over MgSO4
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-ec7ad5e874f14a9e96c22db6cdfd7fb8
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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