Hydrazine hydrate (1:1) → HCID 44118220, compound

HRID 1434729Notes

Reaction equation

HRID 1434729 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:17])[C:8]([CH:10]1[CH2:14][CH2:13][CH:12]([CH3:15])[C:11]1=O)=O)[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[C:10]2[CH2:14][CH2:13][CH:12]([CH3:15])[C:11]=2[NH:3][N:2]=1)=[O:17])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15751935HCID 15751935, compound

Product 1

HCID 44118220HCID 44118220, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.101 mL, 2.05 mmol) was added to a stirring room temperature solution of 4 (0.4055 g, 2.05 mmol) in EtOH (2.0 mL, 1 M) under N2. The reaction was then heated to reflux until judged complete by TLC. The reaction was concentrated and purified by silica gel chromatography (Combiflash column, 96:4 Hexanes:2N NH3 in EtOH): Only pure fractions were combined and concentrated to obtain 0.2003 g (50.4%) of 5. 1H (CDCl3, 400 MHz): δ 9.55 (1H, broad s), 4.35 (2H, q, J=7.1 Hz), 3.26-3.16 (1H, m), 2.89-2.63 (3H, m), 2.09-1.98 (1H, m), 1.37 (3H, t, J=7.2 Hz), 1.30 (3H, d, J=6.9 Hz) ppm. Partial 13C (CDCl3, 100 MHz): δ 128.67, 61.32, 39.73, 32.64, 22.94, 19.62, 14.52 ppm. HPLC: 8.901 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. concentrationThe reaction was concentrated
  4. custompurified by silica gel chromatography (Combiflash column, 96:4 Hexanes:2N NH3 in EtOH)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-079743fa2f654275812d3c8a455cab3d
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

Loading…