Water → HCID 11500257, compound

HRID 2378283Notes

Reaction equation

HRID 2378283 reaction equation
C(OP([CH2:9][C:10]#[N:11])(=O)OCC)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:22][N:23]([CH3:41])[C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:32]2[CH:37]=[CH:36][C:35]([N:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=2)=O)=[CH:26][CH:25]=1.O>C1COCC1>[CH3:22][N:23]([CH3:41])[C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:32]2[CH:37]=[CH:36][C:35]([N:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=2)=[CH:9][C:10]#[N:11])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70314,4'-Bis(dimethylamino)benzophenoneHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 11500257HCID 11500257, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cyanomethylphosphonic acid diethyl ester (1.4 mL, 8.9 mmol) in anhydrous THF (15 mL) was added lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 8.9 mL, 8.9 mmol) at 0° C. and stirred for 30 min at room temperature followed by addition of bis-(4-dimethylamino-phenyl)-methanone (1.19 g, 4.4 mmol) in THF (20 mL) and refluxed overnight. The reaction mixture was poured into water (20 mL), extracted with CH2Cl2 (2×50 mL). The combined organic phases were washed with brine (50 mL), dried over MgSO4, and purified via flash column chromatography (EtOAc/Hexane) to give 3,3-bis-(4-dimethylamino-phenyl)-acrylonitrile as a light yellow needle-like solid (0.75 g, 58% yield): mp, 181-183° C.; 1H NMR (DMSO-d6) δ 2.96 and 2.98 (2s, 6H, 2N(CH3)2), 5.70 (s, 1H, CH), 6.67-6.80 (m, 4H, Ar), 7.15-7.23 (m, 4H, Ar); 13C NMR (DMSO-d6) δ 39.7, 39.8, 87.0, 111.3, 111.4, 120.0, 124.2, 125.6, 129.8, 130.7, 151.0, 151.5, 162.2. Anal. Calcd for C19H21N3: C, 78.32; H, 7.26; N, 14.42. Found: C, 78.33; H, 7.29; N, 14.38.

Workup

  1. temperaturerefluxed overnight
  2. extractionextracted with CH2Cl2 (2×50 mL)
  3. washThe combined organic phases were washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. custompurified via flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-ee29f3b929b7465abb5e9c9afd60d8f0
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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