Diethyl squarate → HCID 10682488, compound

HRID 1733899Notes

Reaction equation

HRID 1733899 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[CH2:11]([O:13][C:14]1[C:15](=O)[C:16](=[O:21])[C:17]=1[O:18]CC)[CH3:12]>C(#N)C.C(OCC)(=O)C>[O:18]=[C:17]1[C:16](=[O:21])[C:15]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[CH3:10])=[C:14]1[O:13][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 123228Diethyl squarate2×HCID 70103164-Amino-3-methylbenzonitrile

Product 1

HCID 10682488HCID 10682488, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-3-methylbenzonitrile (1.94 g, 14.7 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (2.53 g, 14.9 mmol) in acetonitrile (5 mL). After refluxing the mixture for 24 h a second portion of 3,4-diethoxy-3-cyclobutene-1,2-dione (1.15 g, 6.76 mmol) was added and heating was continued for an additional 48 h. The reaction mixture was diluted with ethyl acetate (50 mL), stirred vigorously and filtered free of undissolved solid. The filtrate was chromatographed (CH3OH/CH2Cl2) to afford 0.90 g (24%) of product as a yellow solid: 1H NMR (DMSO-d6): δ 10.50 (s, 1H), 7.76-7.63 (m, 2H), 7.31 (d, 1H), 4.71 (q, 2H), 2.33 (s, 3H), 1.38 (t, 3H).

Workup

  1. additionwas added
  2. temperatureheating
  3. filtrationfiltered free of undissolved solid
  4. customThe filtrate was chromatographed (CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ef141d3ae4ed449594f0132d38705653
Source dataset
uspto-grants-1996_07
Patent number
US05532245

Reaction notes

Loading…