Hydrochloric Acid → HCID 178437742, compound

HRID 259805Notes

Reaction equation

HRID 259805 reaction equation
[NH2:1][C:2]([CH2:9][CH3:10])=[C:3]([Cl:8])[C:4](OC)=[O:5].[CH:11]([NH2:13])=O.C[O-].[Na+].Cl>CO>[Cl:8][C:3]1[C:4]([OH:5])=[N:13][CH:11]=[N:1][C:2]=1[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 713FormamideHCID 10942334Sodium MethoxideHCID 86749529Methyl 3-amino-2-chloro-2-pentenoate

Product 1

HCID 178437742HCID 178437742, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Two dropping funnels are used for simultaneous dropwise addition of a solution of 35.5 g (0.2 mol) of methyl 3-amino-2-chloro-2-pentenoate and 31.5 g (0.7 mol) of formamide in 150 ml of methanol with stirring to 90.3 ml of a 30% strength sodium methylate solution in methanol at room temperature. The mixture is heated slowly to the reflux temperature and left at this for 10 h. After the mixture has cooled, dry HCl gas is passed through the solution until the pH is 3. Evaporation of the solvent is followed by extraction with butanone, drying and evaporation in a rotary evaporator. Yield: 87% [HPLC]

Workup

  1. temperatureThe mixture is heated slowly to the reflux temperature
  2. temperatureAfter the mixture has cooled
  3. customEvaporation of the solvent
  4. extractionis followed by extraction with butanone
  5. customdrying
  6. customevaporation
  7. customin a rotary evaporator

Sources & evidence

ORD record
ord-be3034bc463e4a5893c187c4e0c1b560
Source dataset
uspto-grants-1996_06
Patent number
US05523404

Reaction notes

Loading…