Ethyl Acetate → HCID 54056685, compound

HRID 2379694Notes

Reaction equation

HRID 2379694 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][NH:15][C:16]([C:18]1([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O)=[S:17].C(OCC)(=O)C>O1CCCC1.O>[C:1]([CH:3]=[C:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C:18]1([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[C:16](=[S:17])[NH:15][CH3:14])#[N:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 10922900HCID 10922900, compound

Product 1

HCID 54056685HCID 54056685, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of diethyl cyanomethylphosphonate (215 mg, 1.2 mmol) at room temperature in dry tetrahydrofuran (20 ml) was treated with a 60% oil dispersion of sodium hydride (40 mg, 1 mmol). After 15 mins at room temperature (±)-N-methyl-2-oxo-1-(pyrid-3-yl)cyclohexane carbothioamide (245 mg, 1 mmol) was added and the resulting solution stirred for 3 hours at room temperature. Ethyl acetate (50 ml) and then water (50 ml) were added to the reaction mixture. The layers were separated and the organics washed with water (50 ml). The organic extract was dried over magnesium sulphate and concentrated in vacuo to give a crude gum. Purification by flash chromatography, eluting with a 1:1 (v/v) mixture of ethyl acetate/hexane gave (±)-2-cyanomethylene-N-methyl-1-(pyrid-3-yl)cyclohexane carbothioamide as a colourless gum (190 mg, 0.7 mmol). Trituration with ether yielded a white solid (190 mg, 0.7 mmol), m.p. 182°183° C.;

Workup

  1. customThe layers were separated
  2. washthe organics washed with water (50 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customto give a crude gum
  7. customPurification by flash chromatography
  8. washeluting with a 1:1 (v/v) mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-98fa97f9f2bb4458b687f99b15802126
Source dataset
uspto-grants-1994_11
Patent number
US05364853

Reaction notes

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