Methanol → HCID 178515389, compound

HRID 1881756Notes

Reaction equation

HRID 1881756 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(#N)[CH2:8][C:9]#[N:10].[C:12](=[S:14])=S.CCN(CC)CC.C[OH:23]>CN(C=O)C>[SH:14][C:12]1[C:1]2[CH2:5][CH2:4][CH2:3][C:2]=2[CH:8]=[C:9]([OH:23])[N:10]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6348Carbon DisulfideHCID 8010MalononitrileHCID 8452CyclopentanoneHCID 8471Triethylamine

Product 1

HCID 178515389HCID 178515389, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of cyclopentanone (24 mmol) and malononitrile (24 mmol) in 7.5 mL of MeOH and 1.5 mL of DMF was added 5 mL carbon disulfide followed by the slow addition of 1.5 mL of Et3N. Upon completion of addition, the resulting solution was stirred at RT for 36 h. After this time, the resulting red precipitate was collected by filtration and washed with MeOH. The red solid filter cake was taken up in 50 mL of 1N NaOH. The resulting mixture was stirred at 150° C. for 7 h and then cooled to RT. Once at the prescribed temperature, the resulting red solution was acidified with 6 N HCl. The resulting yellow precipitate was collected by filtration, washed with water and then dried in vacuum to provide the title compound as a red solid (0.35 g, 16%). LC/MS m/z 168 (M+H).

Workup

  1. additionUpon completion of addition
  2. filtrationAfter this time, the resulting red precipitate was collected by filtration
  3. washwashed with MeOH
  4. filtrationThe red solid filter cake
  5. stirringThe resulting mixture was stirred at 150° C. for 7 h
  6. temperaturecooled to RT
  7. filtrationThe resulting yellow precipitate was collected by filtration
  8. washwashed with water
  9. customdried in vacuum

Sources & evidence

ORD record
ord-50ae8b0cb0bc4515948a6bd1a66baa3b
Source dataset
uspto-grants-2012_11
Patent number
US08318941B2

Reaction notes

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