Diethyl squarate → HCID 10590390, compound

HRID 1733897Notes

Reaction equation

HRID 1733897 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[CH2:13]([O:15][C:16]1[C:17](=O)[C:18](=[O:23])[C:19]=1[O:20]CC)[CH3:14]>C(O)C>[CH2:13]([O:15][C:16]1[C:19](=[O:20])[C:18](=[O:23])[C:17]=1[NH:8][C:7]1[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=1)[CH3:14]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 10590390HCID 10590390, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Trifluoromethoxyaniline (5.00 g, 28.2 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (5.00 g, 29.4 mmol) in absolute ethanol (50 mL). The mixture was heated at reflux overnight, then vacuum filtered hot. The filtrate was reduced in volume and the resulting precipitate was filtered to afford 4.50 g (53%) of white solid: mp 145°-146° C.; 1H NMR (DMSO-d6): δ 10.87 (s, 1H), 7.45 (d, 2H), 7.36 (d, 2H), 4.75 (q, 2H), 1.41 (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationvacuum filtered hot
  4. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-9b2aba12f2ff4429b253eb8640d0f3a6
Source dataset
uspto-grants-1996_07
Patent number
US05532245

Reaction notes

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