Hydrazine hydrate (1:1) → 3,6,9,12,15-Pentaoxaheptadecane-1,17-diamine

HRID 1279175Notes

Reaction equation

HRID 1279175 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:23]2C(=O)C3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][NH2:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18427234HCID 18427234, compound

Product 1

HCID 156101913,6,9,12,15-Pentaoxaheptadecane-1,17-diamineYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

The synthesis generally followed the method of Kern et al., Makrol. Chem., 180, 2539 (1979). A solution containing 60 g of 1,17-diphthalimido-3,6,9,12,15-pentaoxaheptadecane (0.118 mol), 14.8 g of hydrazine hydrate (0.296 mol), and 500 mL of ethanol is heated with mechanical stirring in a 100° C. oil bath for three hrs. The mixture is cooled and filtered. A resultant filter cake is washed four times with 300 mL portions of ethanol. The combined filtrates are concentrated to yield 32.35 g of a yellow opaque glassy oil by evaporative distillation at 150-200° C. (0.01 mm of vacuum). The result is 22.82 g of a light yellow oil (69% yield). b.p. 175-177° C. (0.07 mm).

Workup

  1. customThe synthesis
  2. temperatureis heated
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. filtrationA resultant filter cake
  6. washis washed four times with 300 mL portions of ethanol
  7. concentrationThe combined filtrates are concentrated

Sources & evidence

ORD record
ord-5a7066d196a2471487373230fff0da29
Source dataset
uspto-grants-2002_09
Patent number
US06448047B2

Reaction notes

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