Formamide → HCID 178437742, compound

HRID 259804Notes

Reaction equation

HRID 259804 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+]>CO>[Cl:8][C:3]1[C:4]([OH:5])=[N:13][CH:11]=[N:1][C:2]=1[CH2:9][CH3:10]

Participants

5

Reactant 3

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

Product 1

HCID 178437742HCID 178437742, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 163.6 g (1.0 mol) of methyl 3-amino-2-chloro-2-pentenoate, 90.8 g (2.0 mol) of formamide and 150 ml of methanol is added dropwise with stirring to 485.8 ml of a 30% strength NaOMe solution in methanol at room temperature. The mixture is subsequently slowly heated to the reflux temperature over the course of 3 h, and is left to stir at this temperature for a further 12 h. Evaporation of the reaction mixture is followed by dissolving in a little H2O, adjustment to a pH of 3.8 with HCl and extraction with ethyl acetate. Drying over MgSO4 and evaporation provide 177.5 g of crude product which is subsequently recrystallized from water. Yield: 130.4 g (82%)

Workup

  1. additionis added dropwise
  2. temperatureThe mixture is subsequently slowly heated to the reflux temperature over the course of 3 h
  3. waitis left
  4. customEvaporation of the reaction mixture
  5. dissolutionby dissolving in a little H2O, adjustment to a pH of 3.8 with HCl and extraction with ethyl acetate
  6. dry with materialDrying over MgSO4 and evaporation

Sources & evidence

ORD record
ord-8fb098c570834ebfa6e10054028c4e1b
Source dataset
uspto-grants-1996_06
Patent number
US05523404

Reaction notes

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