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

HRID 1073053Notes

Reaction equation

HRID 1073053 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 3 hours. The mixture was then allowed to cool and was then filtered. The filter cake was washed four times with 300 ml portions of ethanol. The combined filtrates were concentrated to give 32.35 g of a yellow opaque glassy oil. Evaporative distillation at 150°-200° C. (0.01 mm) gave 22.82 g of a light yellow oil (69% yield).

Workup

  1. temperaturewere heated
  2. temperatureto cool
  3. filtrationwas then filtered
  4. washThe filter cake was washed four times with 300 ml portions of ethanol
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-ed872cbbc9c846edbff7f315aeb1f378
Source dataset
uspto-grants-1990_11
Patent number
US04968602

Reaction notes

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