Benzoyl chloride → 3'-Nitrobenzanilide

HRID 2086809Notes

Reaction equation

HRID 2086809 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>ClCCl.O>[C:18]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 74233-NitroanilineHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 785033'-Nitrobenzanilide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-nitroaniline (5.95 g) and triethylamine (6.0 ml) in dichloromethane (40 ml) was added dropwise a solution of benzoyl chloride (5.0 ml) in dichloromethane (20 ml). The mixture was stirred at room temperature for 15 minutes, then poured into a mixture of ethyl acetate and water. The organic phase was separated, washed with brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 1-benzoylamino-3-nitrobenzene (9.05 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-45d0cd907f404d48b20c9496266e80b6
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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