Malononitrile → HCID 178469056, compound

HRID 530979Notes

Reaction equation

HRID 530979 reaction equation
O=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C[O:11][CH:12](OC)[N:13](C)C.C(N(CC)CC)C.[C:25](#N)[CH2:26][C:27]#[N:28]>C(O)C.O.C(O)(=O)C>[C:27]([C:26]1[C:12]([OH:11])=[N:13][C:2]([CH3:9])=[C:3]([CH:25]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:28]

Participants

8

Reactant 4

HCID 8010MalononitrileHCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 178469056HCID 178469056, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixed solution of ethyl 3-oxobutanoate (40.0 mL) and N,N-dimethylformamide dimethyl acetal (46.1 mL) in ethanol (80 mL) was stirred at 41° C. to 43° C. for 5 hours. The reaction mixture was cooled to 20° C., and then, triethylamine (4.40 mL) was added thereto. While the reaction mixture was cooled to keep the temperature at 25° C. to 36° C., a mixture of malononitrile (22.9 mL) and ethanol (177 mL) was added dropwise thereto, and the mixture was stirred overnight at room temperature. Acetic acid (21.7 mL) was added to the reaction mixture at 20° C. to 25° C., and then, water (560 mL) was added thereto under heating at 70° C. to 75° C. The reaction mixture was cooled in ice, and then, the deposited solid was collected and washed with water to obtain the title compound (54.8 g).

Workup

  1. temperatureWhile the reaction mixture was cooled
  2. customat 25° C. to 36° C.
  3. additionwas added dropwise
  4. temperatureunder heating at 70° C. to 75° C
  5. temperatureThe reaction mixture was cooled in ice
  6. customthe deposited solid was collected
  7. washwashed with water

Sources & evidence

ORD record
ord-ac0ab02f4b634dfcb825e1512833f3d4
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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