1,2-Dichloroethane → 2',3'-Dimethyl-3-nitrobenzanilide

HRID 1780803Notes

Reaction equation

HRID 1780803 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[CH3:13][C:14]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16].ON1C2C=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:16][C:15]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:14]=1[CH3:13])=[O:9])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 68932,3-DimethylanilineHCID 84973-Nitrobenzoic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 8165712',3'-Dimethyl-3-nitrobenzanilide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-nitrobenzoic acid (3.0 g ) and 2,3-dimethylaniline (2.17 g) in 20 mL of DMF was added 1-hydroxybenzotriazole (2.75 g), EDC (3.44 g) and triethylamine (7.39 mL). The resulting solution was stirred for 16 h. The DMF was evaporated in vacuo and the residue was partitioned with ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solid. NMR (300 MHz, CDCl3) δ 8.72 (1H, s), 8.40 (1 H, d, J=6 Hz), 8.26 (1H, d, J=9 Hz), 7.93 (IH, s), 7.69 (1H, t, J=9 Hz), 7.45 (1 H,d, J=9 Hz), 7.14 (1H, t, J=8 Hz), 7.08 (1H, d, J=9 Hz), 2.32 (3H, s), 2.21 (3H, s).

Workup

  1. customThe DMF was evaporated in vacuo
  2. customthe residue was partitioned with ethyl acetate and water
  3. extractionThe ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a7c0436fc1c4910b757badd95221d5b
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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