Acetonitrile → HCID 20466274, compound

HRID 1904105Notes

Reaction equation

HRID 1904105 reaction equation
C([C:4]([CH:13]([F:15])[F:14])([CH2:10][CH:11]=[CH2:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)N.C(#[N:18])C>O>[NH2:18][C:4]([CH:13]([F:15])[F:14])([CH2:10][CH:11]=[CH2:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 20466273HCID 20466273, compound

Product 1

HCID 20466274HCID 20466274, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of ethyl 2-carbamoyl-2-difluoromethyl-4-pentenoate prepared as in Step B (2.3 g) and iodo-benzene ditrifluoroacetate (3.5 g) in acetonitrile (14 mL) and water (14 mL) is stirred at 80° C. for 16 hours. Water (20 mL) is added and the mixture is extracted with ether (3×20 mL). The aqueous phase is concentrated and the residue suspended in saturated aqueous sodium bicarbonate (10 mL). The suspension is extracted with diethyl ether (3×20 mL). The organic layers are combined, washed with brine, dried over magnesium sulfate and concentrated in vacuo to give ethyl 2-amino-2-difluoromethyl-4-pentenoate (0.6 g) as an oil.

Workup

  1. extractionthe mixture is extracted with ether (3×20 mL)
  2. concentrationThe aqueous phase is concentrated
  3. extractionThe suspension is extracted with diethyl ether (3×20 mL)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f77513d3ebf1440b8b0fbe30955e605e
Source dataset
uspto-grants-1984_03
Patent number
US04439619

Reaction notes

Loading…