1,2-Dichloroethane → 2-amino-N-(3-methylphenyl)benzamide

HRID 1780825Notes

Reaction equation

HRID 1780825 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].ON1C2C=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:15][C:14]1[CH:16]=[CH:17][CH:18]=[C:12]([CH3:11])[CH:13]=1)=[O:6]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 227Anthranilic AcidHCID 7934m-ToluidineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 24673682-amino-N-(3-methylphenyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-aminobenzoic acid (290 mg) and 3-methylaniline (215 mg) in 10 mL of DMF was added 1-hydroxybenzotriazole (300 mg), EDC (400 mg) and triethylamine (500 μL). The resulting solution was stirred for 16 h. The reaction solution was partitioned with ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 5% citric acid, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solid.

Workup

  1. customThe reaction solution was partitioned with ethyl acetate and water
  2. extractionThe ethyl acetate layer was extracted w/50 mL each of 5% citric acid, saturated sodium bicarbonate, saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4271616932c4e29a9f6fca2fb3aeda0
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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