Ethyl orthoformate → 2-cyano-N-cyclohexyl-3-ethoxy-prop-2-enamide

HRID 1160526Notes

Reaction equation

HRID 1160526 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5])#[N:2].[CH:13](OCC)(OCC)[O:14][CH2:15][CH3:16]>C(OC(=O)C)(=O)C>[C:1]([C:3](=[CH:13][O:14][CH2:15][CH3:16])[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 7061432-Cyano-N-cyclohexylacetamide2×

Product 1

HCID 670194772-cyano-N-cyclohexyl-3-ethoxy-prop-2-enamideYield 35.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2-cyano-N-cyclohexyl-acetamide (Intermediate #18) (1.35 g, 8.09 mmol) was suspended in acetic anhydride (20 mL). Triethyl orthoformate (3.91 g, 21 mmol) was added and the mixture heated to reflux for 5 h. The reaction mixture was cooled to ambient and volatiles removed by evaporation in vacuo to leave a brown oil which was which was purified by chromatography on silica gel eluting with an EtOAc/DCM gradient (0-10%) to give the title compound as a solid (637 mg, 35%)

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 5 h
  3. temperatureThe reaction mixture was cooled to ambient and volatiles
  4. customremoved by evaporation in vacuo
  5. customto leave a brown oil which
  6. customwas purified by chromatography on silica gel eluting with an EtOAc/DCM gradient (0-10%)

Sources & evidence

ORD record
ord-5446c6dc5d094c01b7f4e475e4f95c8d
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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