Malononitrile → HCID 69215495, compound

HRID 900160Notes

Reaction equation

HRID 900160 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22].[C:29](#[N:33])[CH2:30][C:31]#[N:32]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:33][C:29]1[N:22]([CH2:21][C:20]2[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:19]=2[O:18][CH3:17])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:30]=1[C:31]#[N:32]

Participants

6

Reactant 3

HCID 8010MalononitrileHCID 8400BenzoinHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 69215495HCID 69215495, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzoin (6.81 g, 32.1 mmol), 2,4-dimethoxybenzylamine (5.37 g, 32.1 mmol) and p-toulenesulfonic acid monohydrate (20 mg, cat.) in toluene (100 mL) was heated to 80° C. for 5 minutes. Malononitrile (2.12 g, 32.1 mmol) was then added and the reaction mixture was heated to reflux for 3 hours using a reflux condenser fitted with a Dean-Stark trap. The solution was then cooled, diluted with ethyl acetate (100 mL), extracted with sodium bicarbonate (conc., aq., 50 mL), hydrochloric acid (0.5N, aq., 50 mL) and water (50 mL), dried, filtered and the filtrate was concentrated under reduced pressure. Chromatography (SiO2, ethyl acetate:hexane 1:2) afforded the title compound as a pale brown solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customfitted with a Dean-Stark trap
  4. temperatureThe solution was then cooled
  5. extractionextracted with sodium bicarbonate (conc., aq., 50 mL), hydrochloric acid (0.5N, aq., 50 mL) and water (50 mL)
  6. customdried
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-55049057fc7f459db02e056aaef99b18
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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