Malononitrile → HCID 178450345, compound

HRID 1297507

Reaction equation

HRID 1297507 reaction equation
C(O[C:6]1[C:7](=[O:16])[C:8](=[O:15])[C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14])CCC.[CH2:17]([C:20]#[N:21])[C:18]#[N:19].[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH3:23]>C1C=CC=CC=1>[CH2:11]([O:10][C:9]1[C:6](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[C:7](=[O:16])[C:8]=1[O-:15])[CH2:12][CH2:13][CH3:14].[CH2:22]([NH+:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH3:23]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 65108Dibutyl squarate

Product 1

HCID 178450345HCID 178450345, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2.16 ml (10 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (2b) was dissolved in 20 ml of anhydrous benzene, and 660 mg (10 mmol) of malonodinitrile was added under stirring. Then, 1.65 ml (12 mmol) of triethylamine was added dropwise for 5 min followed by 10 ml of anhydrous benzene. The obtained emulsion is stirred for 30 min at room temperature. The solvent is removed using a rotary evaporator. The yellow oiled residue is treated three times with ether to give crude product 2d (1.8 g, 56%), 1H-NMR (DMSO-d6): δ 10.15–9.55 (1H, broad s, NH+), 4.59 (2H, t, 6.7 Hz, OCH2), 3.07 (6H, q 7.4, 14.5 Hz, N(CH2CH3)3), 1.77–1.58 (2H, m, CH2), 1.48–1.26 (2H, m, CH2), 1.18 (9H, t, 7.3 Hz, N(CH2CH3)3), 0.90 (3H, t, 7.4 Hz, CH3).

Workup

  1. stirringThe obtained emulsion is stirred for 30 min at room temperature
  2. customThe solvent is removed
  3. customa rotary evaporator
  4. additionThe yellow oiled residue is treated three times with ether

Sources & evidence

ORD record
ord-e2e5d3fab79d4541a316c228b7dd659f
Source dataset
uspto-grants-2007_07
Patent number
US07250517B2

Linked notes

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