Aziridine → 3-(Aziridin-1-yl)-4-nitrobenzamide

HRID 1058507Notes

Reaction equation

HRID 1058507 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH2:7])=[O:6].[NH:14]1[CH2:16][CH2:15]1>CC#N>[N:14]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[N+:11]([O-:13])=[O:12])[C:5]([NH2:7])=[O:6])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 9033AziridineHCID 114239673-Fluoro-4-nitrobenzamide

Product 1

HCID 112757783-(Aziridin-1-yl)-4-nitrobenzamideYield 41.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of the above benzamide (100 mg, 0.54 mmol) in dry MeCN (4 mL) was treated with aziridine (168 μL, 3.24 mmol) at room temperature for 4 h. The resulting precipitate was collected, washed with cold water, and crystallized twice from EtOAc to give 9 (46 mg, 41%). mp 223-224° C.;; 1H NMR [(CD3)2SO] δ8.21 (br s, 1H, NHH), 7 99 (d, J=8.5 Hz, 1H, H-5), 7.69 (d, J=1.8 Hz, 1H, H-2), 7.67 (br s, 1H, NHH), 7.56 (dd, J=8 5, 1.8 Hz, 1H, H-6), 2.30 (s, 4H, (CH2)2). Anal. Calcd for C9H9N3O3: C, 52.17;H, 4.38, N, 20.28. Found C, 52 10;H, 4.30, N, 20.07%.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with cold water
  3. customcrystallized twice from EtOAc

Sources & evidence

ORD record
ord-cc89bedd1ada410b8cff13ac70bd83d0
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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