Hydrazine hydrate (1:1) → HCID 57561766, compound

HRID 1366872Notes

Reaction equation

HRID 1366872 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:18])[C:8]([CH:10]1[CH2:14][CH2:13][C:12]([CH3:16])([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][C:12]([CH3:16])([CH3:15])[C:11]=2[NH:3][N:2]=1)=[O:18])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57435070HCID 57435070, compound

Product 1

HCID 57561766HCID 57561766, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.229 mL, 4.71 mmol) was added to a stirring room temperature solution of 1 (0.9961 g, 4.71 mmol) in EtOH (4.7 mL, 1 M) under N2. The reaction was then heated to reflux until judged complete by TLC (2 h). The reaction was concentrated and purified by silica gel chromatography (Combiflash column, 70:30:2 Hexanes:CH2Cl2:2N NH3 in EtOH). Only pure fractions were combined and concentrated to obtain 0.6955 g (71.2%) of 2. 1H (CDCl3, 400 MHz): δ 11.04 (1H, broad s), 4.33 (2H, q, J=7.3 Hz), 2.76 (2H, t, J=6.8 Hz), 2.26 (2H, t, J=6.8 Hz), 1.33 (3H, t, J=7.3 Hz), 1.31 (6H, s) ppm. 13C (CDCl3, 100 MHz): δ 168.08, 160.61, 128.73, 127.27, 61.15, 47.22, 38.64, 27.57, 22.00, 14.48 ppm.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. customuntil judged complete by TLC (2 h)
  4. concentrationThe reaction was concentrated
  5. custompurified by silica gel chromatography (Combiflash column, 70:30:2 Hexanes:CH2Cl2:2N NH3 in EtOH)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-80236601136f45e198fb8cb4f0792812
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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