Acetonitrile → HCID 67492224, compound

HRID 1921571Notes

Reaction equation

HRID 1921571 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]1[NH:7][CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2].[O:11]=[C:12]([CH:14]=[C:15]([CH3:17])[CH3:16])[CH3:13].[CH2:18]1[CH2:28][CH2:27]N2[C:21](=NCCC2)[CH2:20][CH2:19]1.[CH3:29]C#N>C(OCC)(=O)C>[CH3:29][C:21]1[CH:20]=[CH:19][C:18]([C:10]2[CH:9]=[CH:8][NH:7][C:6]=2[CH2:5][CH:4]([N+:1]([O-:3])=[O:2])[C:15]([CH3:17])([CH3:16])[CH2:14][C:12](=[O:11])[CH3:13])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8858Mesityl oxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10534737nitroethyl pyrrole

Product 1

HCID 67492224HCID 67492224, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following a standard procedure (Ptaszek et al., supra), a mixture of 3 (460 mg, 2.00 mmol) and mesityl oxide (458 μL, 4.00 mmol) in CH3CN (4.0 mL) was treated with DBU (897 μL, 6.00 mmol). The reaction mixture was stirred for 24 h at room temperature, diluted with ethyl acetate (15.0 mL) and washed with water and brine. The organic layer was dried (Nk2SO4) and concentrated. Excess mesityl oxide was removed under high vacuum. The resulting oil was chromatographed [ethyl acetate/hexanes (1:2)] to afford a light brown oil (486 mg, 74%): 1H NMR δ 1.08 (s, 3H), 1.19 (s, 3H), 2.10 (s, 3H), 2.37 (s, 3H), 2.37, 2.55 (AB, 2J=17.6 Hz, 2H), 3.21 (ABX, 3J=2.6 Hz, 2J=15.6 Hz, 1H), 3.38 (ABX, 3J=11.6 Hz, 2J=15.6 Hz, 1H), 5.18 (ABX, 3J=2.6 Hz, 3J=11.6 Hz, 1H), 6.22-6.24 (m, 1H), 6.67-6.69 (m, 1H), 7.20 (d, J=8.0 Hz, 2H), 7.24 (d, J=8.0 Hz, 2H), 8.05-8.20 (br, 1H).

Workup

  1. washwashed with water and brine
  2. customThe organic layer was dried (Nk2SO4)
  3. concentrationconcentrated
  4. customExcess mesityl oxide was removed under high vacuum
  5. customThe resulting oil was chromatographed [ethyl acetate/hexanes (1:2)]

Sources & evidence

ORD record
ord-e21ba285cba74bb8a1bbe992c5e02b43
Source dataset
uspto-grants-2012_05
Patent number
US08173692B2

Reaction notes

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