Nitroethane → HCID 68527591, compound

HRID 1036376Notes

Reaction equation

HRID 1036376 reaction equation
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH2:9]([N:11](CC)CC)[CH3:10].C1(N=C=[O:24])C=CC=CC=1.[N+](CC)([O-])=O>C1(C)C=CC=CC=1>[CH3:10][C:9]1[CH:2]2[C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH:1]2[O:8][N:11]=1

Participants

6

Reactant 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 707232-Cyclohepten-1-one

Product 1

HCID 68527591HCID 68527591, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 80% technical grade 2-cycloheptenone (3.48 mL, 25 mmol) and triethylamine (1 mL) in toluene were added phenylisocyanate (5.95 g, 50 mmol) and nitroethane (2.24 g, 30 mmol) in four portions over 1 hour. The reaction mixture was stirred at ambient temperature for 4 hours, the precipitate was filtered off and the filtrate was concentrated. The obtained residue was chromatographed, eluting with 20% ethyl acetate/hexane to yield the title compound: 1H NMR (300 MHz, CDCl3) δ 4.81 (m, 1 H), 4.06 (d, J=11.87 Hz, 1 H), 2.47 (m, 2 H), 2.02 (m, 3 H), 1.93 (m, 2 H), 1.81 (m, 2 H), 1.67 (m, 2 H); MS (DCI/NH3) m/z 168 (M+H)+.

Workup

  1. filtrationthe precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was chromatographed
  4. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2462051d1df64fe3b7c730616b25980b
Source dataset
uspto-grants-2013_10
Patent number
US08546410B2

Reaction notes

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