Ammonia → 3-Amino-4-n-butoxy-3-cyclobutene-1,2-dione

HRID 2257373Notes

Reaction equation

HRID 2257373 reaction equation
[NH3:1].[CH3:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:11](=[O:12])[C:9](=[O:10])[C:8]=1OCCCC>CCOCC>[NH2:1][C:8]1[C:9](=[O:10])[C:11](=[O:12])[C:7]=1[O:6][CH2:5][CH2:4][CH2:3][CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 65108Dibutyl squarate

Product 1

HCID 145450343-Amino-4-n-butoxy-3-cyclobutene-1,2-dioneYield 92.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ammonia gas was bubbled into a solution of dibutyl squarate (22.6 g, 100 mmol) in ether (500 mL) contained in a 1 L three-necked, round-bottomed flask equipped with a mechanical stirrer and an acidic scrubber. Precipitation of product ceased after 3 hours, so the reaction was halted and the ether solution was filtered. The solid residue was washed with ether and set aside. The filtrate was allowed to stand at room temperature for a further 3 hours, after which time more solid was observed to have been precipitated. This solid was collected by filtration, washed with ether, and combined with the material set aside previously. Drying in vacuo afforded the product as a white solid (15.7 g, 92.9% yield). The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. customround-bottomed flask equipped with a mechanical stirrer
  2. customPrecipitation of product
  3. filtrationthe ether solution was filtered
  4. washThe solid residue was washed with ether
  5. waitto stand at room temperature for a further 3 hours
  6. customto have been precipitated
  7. filtrationThis solid was collected by filtration
  8. washwashed with ether
  9. customDrying in vacuo

Sources & evidence

ORD record
ord-c3d9be4682854f9e870bacb6880d7d12
Source dataset
uspto-grants-1997_08
Patent number
US05656750

Reaction notes

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