Water → HCID 13294557, compound

HRID 1926863Notes

Reaction equation

HRID 1926863 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:19](#[N:23])[CH2:20][C:21]#[N:22].C(NCC)C.O>CN(C=O)C>[NH2:23][C:19]1[O:1][C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[C:20]=1[C:21]#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 37914-METHOXYBENZOINHCID 8010MalononitrileHCID 8021Diethylamine

Product 1

HCID 13294557HCID 13294557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 236 g (974 mmol) 2-hydroxy-1-(4-methoxyphenyl)-2-phenylethanone and 83.66 g (1266 mmol) malononitrile in 470 ml DMF and, with cooling on an ice bath, add 86.6 ml (836.7 mmol) diethylamine. After 1 h, heat the mixture to RT and continue stirring for 4 h at RT, before adding 2.5 litre water and a few seed crystals. After 30 min, decant the supernatant water and replace with 1.25 litre of fresh water. Stir the suspension thoroughly and again decant the supernatant water. Take up the sticky crystalline residue in ethyl acetate and then concentrate under vacuum almost completely. Stir the residue with 730 ml diisopropyl ether and leave the suspension to stand overnight at RT. Then filter off the solid matter with suction and dry under vacuum. 211.5 g (57.6% of theor.) of the title compound is obtained.

Workup

  1. temperaturewith cooling on an ice bath
  2. waitAfter 30 min
  3. customdecant the supernatant water
  4. stirringStir the suspension thoroughly
  5. customagain decant the supernatant water
  6. concentrationconcentrate under vacuum almost completely
  7. stirringStir the residue with 730 ml diisopropyl ether
  8. customleave the suspension
  9. waitto stand overnight at RT
  10. filtrationThen filter off the solid matter with suction
  11. customdry under vacuum

Sources & evidence

ORD record
ord-6ab448d2cb994ad7929d538fbf80f862
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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