Hydrazine → HCID 175538, compound

HRID 1895828Notes

Reaction equation

HRID 1895828 reaction equation
[OH:1][CH:2]([CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[N+:21]([O-:23])=[O:22])[CH2:3][N:4]1C(=O)C2C(=CC=CC=2)C1=O.NN>C(O)C.O>[NH2:4][CH2:3][CH:2]([OH:1])[CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 3373341-(3-Phthalimido-2-hydroxy propyl)-2-nitroimidazole

Product 1

HCID 175538HCID 175538, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Compound 8 (5 g, 15.8 mmol) was added to a solution of pure hydrazine (608 mg, 18.97 mmol, 1.2 equivalent) in 50 ml of ethyl alcohol and 4 ml of water. The mixture was refluxed for 2 h and then held at room temperature. The white solid (phthalhydrazide) was filtered. The filtrate was concentrated and the residue was redistributed in ethyl acetate and water. The water phase was extracted two times with ethyl acetate and the combined ethyl acetate phase was dried to give a yellowish solid as the HCl salt (9, 2.45 g, 70% yield). 1H NMR (D2O, δppm) (HCl salt): 2.91 (dd, 1H, NH2—CHa, J=13.2 Hz, 9.9 Hz), 3.21 (dd, 1H, NH2—CHb, J=13.2 Hz, 2.7 Hz), 4.19 (tt, 1H, HO—CH—, J=9.0 Hz, 3.0 Hz), 4.28 (dd, 1H, imidazole-CHa—, J=13.8 Hz, 8.7 Hz), 4.57 (dd, 1H, imidazole-CHb—, J=13.8 Hz, 2.7 Hz), 7.09 (d, 1H, J=0.9 Hz, —CH═), 7.35 (d, 1H, J=0.9 Hz, —CH═). 13C NMR (D2O, δppm). 42.06, 53.00, 66.86, 128.06, 128.92, 144.73.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customheld at room temperature
  3. filtrationThe white solid (phthalhydrazide) was filtered
  4. concentrationThe filtrate was concentrated
  5. extractionThe water phase was extracted two times with ethyl acetate
  6. dry with materialthe combined ethyl acetate phase was dried

Sources & evidence

ORD record
ord-a2e4868a8be8457cb368e31c8abaee5b
Source dataset
uspto-grants-2013_08
Patent number
US08518371B2

Reaction notes

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