Sodium Acetate → HCID 178470743, compound

HRID 1603706Notes

Reaction equation

HRID 1603706 reaction equation
F[B-](F)(F)F.C(S[N:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])C.Cl.[NH2:17][CH2:18][C:19](=O)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:24]([O:23][C:21]([CH2:20][C:19]1[N:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:17][CH:18]=1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 13086678HCID 13086678, compoundHCID 86754833HCID 86754833, compound

Product 1

HCID 178470743HCID 178470743, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.5 g of ethyl (ethylthio)iminoacetate tetrafluoroborate, 110 ml of acetic acid, 1.8 g of ethyl 4-aminoacetoacetate hydrochloride and 1.64 g of sodium acetate is heated for 3 hours at a temperature close to 95° C. The reaction mixture is filtered and the insoluble matter is rinsed with 3×5 ml of acetic acid. The filtrate is evaporated in a rotary evaporator and the evaporation residue is supplemented with 75 ml of dichloromethane. The organic solution is dried over sodium sulphate, filtered and evaporated in a rotary evaporator. The evaporation residue (1.86 g) is purified by chromatography on a silica column, eluting with ethyl acetate. 1.5 g of ethyl 4-(ethoxycarbonylmethyl)imidazole-2-carboxylate are obtained in the form of a red-yellow solid melting at 88° C.

Workup

  1. temperatureis heated for 3 hours at a temperature
  2. customclose to 95° C
  3. filtrationThe reaction mixture is filtered
  4. washthe insoluble matter is rinsed with 3×5 ml of acetic acid
  5. customThe filtrate is evaporated in a rotary evaporator
  6. dry with materialThe organic solution is dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in a rotary evaporator
  9. customThe evaporation residue (1.86 g) is purified by chromatography on a silica column
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c963d74eb0ec4ee1af85520dbe8edcea
Source dataset
uspto-grants-1999_11
Patent number
US05990108

Reaction notes

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