Aniline → 3-chloro-4-nitro-N-phenyl-benzamide

HRID 1773575Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[C:14]([OH:16])=O.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[C:14]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

Diisopropylethylamine (0.65 mL, 3.7 mmol) was added to a mixture of 3-chloro-4-nitro-benzoic acid (0.2 g, 0.992 mmol), aniline (0.1 mL, 1.1 mmol) and HBTU (0.42 g, 1.1 mmol) in acetonitrile (20 mL) and the reaction mixture was stirred at 80° C. for 8 hours and then at room temperature for 62 hours. The resulting mixture was then partitioned between water and ethyl acetate, the organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug (hexane/EtOAc, 80/20) to afford 135 mg (49% yield) of 3-chloro-4-nitro-N-phenyl-benzamide as a yellow solid.

Workup

waitat room temperature for 62 hours
customThe resulting mixture was then partitioned between water and ethyl acetate
customthe organic layer was separated
extractionthe aqueous layer was extracted twice with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe crude residue was purified on a silica gel plug (hexane/EtOAc, 80/20)

Sources & evidence

ORD record: ord-b121c69b0db943ec91179024493f9fe3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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