Malononitrile → 4-(4-Acetamidophenyl)-2-amino-3-cyanofurane

HRID 32472Notes

Reaction equation

HRID 32472 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][OH:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:15](#[N:19])[CH2:16][C:17]#[N:18].C(NCC)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]#[N:18])=[C:15]([NH2:19])[O:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8010MalononitrileHCID 8021DiethylamineHCID 221825304'-Acetamido-2-hydroxyacetophenone

Product 1

HCID 692077374-(4-Acetamidophenyl)-2-amino-3-cyanofuraneYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4′-acetamido-2-hydroxyacetophenone 4 (7.17 g, 39 mmol) in DMF (65 mL), malononitrile (2.84 g, 43 mmol) was added. With cooling in an ice-water bath, diethylamine (6.05 mL 59 mmol) was gradually added within 20 min. The mixture was stirred at room temperature for 2 h and then diluted with ethyl acetate (400 mL). The mixture was washed with brine (3×200 mL), dried over sodium sulfate, and then evaporated in vacuo. Residual material was treated with dichloromethane and n-hexane, concentrated in vacuo, and precipiated in the concentrated mixture. The precipitated material was filtrated and washed with n-hexane to give 5 (7.64 g) as a brown solid. MS(ES) m/e 242 [M+H].

Workup

  1. temperatureWith cooling in an ice-water bath
  2. washThe mixture was washed with brine (3×200 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. additionResidual material was treated with dichloromethane and n-hexane
  6. concentrationconcentrated in vacuo
  7. filtrationThe precipitated material was filtrated
  8. washwashed with n-hexane

Sources & evidence

ORD record
ord-05dc8754f7b14f1a88d7ffae8bbf4299
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Reaction notes

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