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

HRID 2226358Notes

Reaction equation

HRID 2226358 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

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 were heated with mechanical stirring in a 100° C. oil bath for three hours. The mixture was then cooled and filtered. The resultant filter cake was washed four times with 300 ml portions of ethanol. The combined filtrates were concentrated to yield 32.35 g of a yellow opaque glassy oil. The evaporative distillation at 150°-200° C. (0.01 mm) gave 22.82 g of a light yellow oil (69% yield). lit. b.p. 175°-177° C. (0.07 mm).

Workup

  1. temperaturewere heated
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. filtrationThe resultant filter cake
  5. washwas washed four times with 300 ml portions of ethanol
  6. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-fa3fe3267ef545b7bb486389bdedb754
Source dataset
uspto-grants-1994_09
Patent number
US05348855

Reaction notes

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