Malononitrile → HCID 89407689, compound

HRID 588745Notes

Reaction equation

HRID 588745 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].C(N(CC)CC)C.[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C1COCC1.C1(C)C=CC=CC=1>[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:19])=[C:2]([C:1]#[N:5])[C:3]#[N:4])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 89407689HCID 89407689, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

To a solution of malononitrile (30 mmol) and triethylamine (36 mmol) in THF/toluene (40 mL, 1:1) at 0° C. was slowly added 4-fluorobenzoyl chloride (30 mmol). The resulting reaction mixture was stirred at room temperature for 2 hours. After concentration under reduced pressure, the crude residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1:30), yielding the pure title compound (5.2 g, 93%) as a yellowish oil. MS (m/z) 189.2 [M+H]+ (100%). δH (300 MHz, CDCl3, 25° C.) 10.61 (br s, 1H), 7.80 (dd, J 8.7, 5.4 Hz, 2H), 7.06 (t, J 8.7 Hz, 2H).

Workup

  1. customat 0° C.
  2. customThe resulting reaction mixture
  3. concentrationAfter concentration under reduced pressure
  4. customthe crude residue was purified by flash chromatography on silica
  5. additiona mixture of methanol and dichloromethane (in a ratio of 1:30),

Sources & evidence

ORD record
ord-36da882c1133472eae9d073a73097ea6
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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