Malononitrile → HCID 86671851, compound

HRID 573575Notes

Reaction equation

HRID 573575 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[CH3:10][C:11]1[CH:12]=[C:13]([C:17](=O)[CH3:18])[CH:14]=[CH:15][CH:16]=1.[C:20](#[N:24])[CH2:21][C:22]#[N:23]>C(O)(=O)C.O>[CH3:10][C:11]1[CH:12]=[C:13]([C:17](=[C:21]([C:20]#[N:24])[C:22]#[N:23])[CH3:18])[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8010MalononitrileHCID 114553-MethylacetophenoneHCID 13838Hexamethyldisilazane

Product 1

HCID 86671851HCID 86671851, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of acetic acid (10 mL) was added dropwise hexamethyldisilazane (3.89 mL, 18.65 mmol) over ca. 30 min with the temperature kept below 40° C. throughout the addition. This resulting solution was subsequently added to a stirred solution of 1-(3-methylphenyl)ethanone (2.03 mL, 14.91 mmol) and malononitrile (1.88 mL, 29.8 mmol) in acetic acid (10 mL) and the mixture heated to 70° C. under nitrogen overnight. The reaction mixture was then cooled to RT, diluted with water (ca. 50 mL) and extracted with toluene (ca. 50 mL×2). The combined organic layer was passed through a phase separator and the solvent concentrated in vacuo, to give the title compound (2.89 g) which was used in next step without further purification. LCMS (A) m/z: 181 [M−1]−, Rt 1.23 min (acidic).

Workup

  1. additionkept below 40° C. throughout the addition
  2. temperatureThe reaction mixture was then cooled to RT
  3. extractionextracted with toluene (ca. 50 mL×2)
  4. concentrationthe solvent concentrated in vacuo

Sources & evidence

ORD record
ord-98dc8e0420d94c579ed3959d57e60a89
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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