2-Nitroimidazole → HCID 178427301, compound

HRID 729202Notes

Reaction equation

HRID 729202 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[S:9]([CH2:19][CH2:20][CH2:21]S(C1C=CC(C)=CC=1)(=O)=O)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>CN(C=O)C>[S:9]([CH2:19][CH2:20][CH2:21][C:6]1[N:5]=[C:4]([N+:1]([O-:3])=[O:2])[NH:8][CH:7]=1)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 107012-NitroimidazoleHCID 1483198HCID 1483198, compound

Product 1

HCID 178427301HCID 178427301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture containing 2-nitroimidazole (1 g, 8.34 mmol) and Cs2,CO3 (2.9 g, 8.90 mmol) in dimethylformaide (DMF, 50 ml), 1,3-ditosylpropane (3.84 g, 9.99 mmol) was added. The reaction was heated at 80° C. for 3 hours. The solvent was evaporated under vacuum and the residue was suspended in ethylacetate. The solid was filtered, the solvent was concentrated, loaded on a silica gel-packed column and eluted with hexane:ethylacetate (1:1). The product, 3-tosylpropyl-(2-nitroimidazole), was isolated (1.67 g, 57.5%) with m.p. 108-111° C. 1H-NMR (CDCl3) δ 2.23 (m, 2H), 2.48 (S, 3H), 4.06 (t, 2H, J=5.7 Hz), 4.52 (t, 2H, J=6.8 Hz), 7.09 (S, 1H), 7.24 (S, 1H), 7.40 (d, 2H, J=8.2 Hz), 7.77 (d, 2H, J=8.2 Hz).

Workup

  1. additionwas added
  2. customThe solvent was evaporated under vacuum
  3. filtrationThe solid was filtered
  4. concentrationthe solvent was concentrated
  5. washeluted with hexane:ethylacetate (1:1)

Sources & evidence

ORD record
ord-22c82afce8d54930a866fb61ee4a8c3d
Source dataset
uspto-grants-2009_09
Patent number
US07582281B2

Reaction notes

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