Malononitrile → HCID 178450345, compound

HRID 2218533Notes

Reaction equation

HRID 2218533 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 (200 MHz, DMSO-d6), δ, ppm: 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-36a116864a5b48e39ba17bee3ac02008
Source dataset
uspto-grants-2008_08
Patent number
US07411068B2

Reaction notes

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