2-Methoxyprop-2-enenitrile → 685094-19-3

HRID 1191094Notes

Reaction equation

HRID 1191094 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)#[N:3].CO[C:14](=[CH2:17])[C:15]#[N:16].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[NH2:16][C:15]1[CH:14]=[CH:17][N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[CH:5][CH:6]=2)[N:11]=1

Participants

5

Reactant 3

HCID 132442492-Methoxyprop-2-enenitrileHCID 162129624-Cyanophenylhydrazine HydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 42656760685094-19-3

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Suspend 4-cyanophenyl hydrazine hydrochloride (5 g, 29.58 mmol) in tert-butanol (60 mL). Add methoxyacrylonitrile (2.458 g, 29.58 mmol) and potassium tert-butoxide (3.975 g, 35.49 mmol) and heat the mixture at 90° C. overnight. Concentrate in vacuo and partition the residue between EtOAc/water. Extract the organic phase with 10% hydrochloric acid. Neutralize the aqueous phase with saturated aqueous NaHCO3 and extract twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain a solid that was washed with ether/hexane. Filter and dry the solid in vacuo to obtain the desired intermediate.

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between EtOAc/water
  3. extractionExtract the organic phase with 10% hydrochloric acid
  4. extractionNeutralize the aqueous phase with saturated aqueous NaHCO3 and extract twice with EtOAc
  5. dry with materialDry the combined organic extracts over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a solid
  9. washthat was washed with ether/hexane
  10. filtrationFilter
  11. customdry the solid in vacuo

Sources & evidence

ORD record
ord-ad60509a178c4cb99bf27bc702de3bb6
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…