Aniline → 2-chloro-5-methoxy-4-nitro-N-phenyl-benzamide

HRID 1773502Notes

Reaction equation

HRID 1773502 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(O[N:24]1N=N[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=CC=CC=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:6]

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580563702-Chloro-5-methoxy-4-nitrobenzoic acid

Product 1

HCID 666645802-chloro-5-methoxy-4-nitro-N-phenyl-benzamideYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-5-methoxy-4-nitro-benzoic acid (200 mg, 0.86 mmol) in acetonitrile (10 mL) was added HBTU (327 mg, 0.86 mmol) followed by aniline (0.08 mL, 0.86 mmol) and diisopropylethylamine (0.56 mL, 3.20 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then heated at 60° C. for 24 hours and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL); the organic layer was separated and washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 75/25) to give 182 mg of 2-chloro-5-methoxy-4-nitro-N-phenyl-benzamide as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was then heated at 60° C. for 24 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
  4. customthe organic layer was separated
  5. washwashed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 75/25)

Sources & evidence

ORD record
ord-ed72ed03b3ea4045b2691bc3d25425f2
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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