Squaric acid → HCID 178426355, compound

HRID 485731

Reaction equation

HRID 485731 reaction equation
[C:1]1(O)[C:5](=[O:6])[C:3](=O)[C:2]=1[OH:7].[NH2:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1>C(O)(C)C>[CH3:16][C:14]1([CH3:17])[CH2:15][CH:10]([NH:9][C+:1]2[C:2]([O-:7])=[C:3]([NH:9][CH:10]3[CH2:11][C:12]([CH3:19])([CH3:18])[NH:13][C:14]([CH3:17])([CH3:16])[CH2:15]3)[C+:5]2[O-:6])[CH2:11][C:12]([CH3:19])([CH3:18])[NH:13]1

Participants

4

Reactant 2

HCID 17913Squaric acidHCID 375244-Amino-2,2,6,6-tetramethylpiperidine

Product 1

HCID 178426355HCID 178426355, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In an autoclave, 114.0 g of quadratic acid (1.0 mole), 390.8 g of 4-amino-2,2,6,6-tetramethylpiperidine (2.5 moles), and 800 cc of isopropanol were heated for five hours to 140° C. and then for 15 hours to 210° C. After cooling, the solid was suctioned off and dried. The thusobtained crude product was eluted three times with boiling methanol, washed with cold methanol, and then exhaustively dried, yielding as the remainder 353.1 g of white crystals (yield: 90.4%, mp>400° C., decomposition).

Workup

  1. temperatureAfter cooling
  2. customdried
  3. washwas eluted three times with boiling methanol
  4. washwashed with cold methanol
  5. customexhaustively dried

Sources & evidence

ORD record
ord-faed4478198f48718faf6c2e10510a16
Source dataset
uspto-grants-1985_08
Patent number
US04537924

Linked notes

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