Dimethylamine, hydrochloride → 5-Chloro-N,N-dimethyl-2-nitrobenzamide

HRID 423280Notes

Reaction equation

HRID 423280 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([CH:12]=1)C(O)=O)([O-:3])=[O:2].C1C=C2N=NN([OH:23])C2=CC=1.O.Cl.C(N=C=NC1[C:36]([N:37]([CH3:39])[CH3:38])=CC=CN=1)C.Cl.CNC>CN(C=O)C.O.C(N(CC)CC)C>[Cl:13][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[C:12]([CH:8]=1)[C:36]([N:37]([CH3:39])[CH3:38])=[O:23]

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 172872-Chloro-5-nitrobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 866046491-Ethyl-3-(3-dimethylaminopyridyl)carbodiimide hydrochloride

Product 1

HCID 229348075-Chloro-N,N-dimethyl-2-nitrobenzamideYield 99.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 5-nitro-2-chlorobenzoic acid (1 g), 1-hydroxybenzotriazolemonohydrate (1.14 g) and 1-ethyl-3-(3-dimethylaminopyridyl)carbodiimide hydrochloride (1.42 g) in N,N′-dimethylformamide (10 mL) were added dimethylamine hydrochloride (0.61 g) and triethylamine (1 mL). The mixture was stirred for all day and night, and then water was added. The reaction solution was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and concentrated to give the title compound (1.13 g).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c4a91d34cf9642a8aa5db3a87e3ec82b
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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