Hydrochloric Acid → HCID 178494677, compound

HRID 1586703Notes

Reaction equation

HRID 1586703 reaction equation
[H-].[Na+].[CH2:3]([O:5]C=O)[CH3:4].[H][H].Cl.[CH3:11][O:12][CH2:13][C:14]([NH2:16])=[NH:15].Cl.[CH:18](OC(C)C)(C)C>O.C(OCC)(=O)C>[OH:5][C:3]1[CH:4]=[CH:18][N:16]=[C:14]([CH2:13][O:12][CH3:11])[N:15]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 135486022-Methoxyethanimidamide hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 178494677HCID 178494677, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, 31.5 g (0.72 mol) of sodium hydride are suspended in 690 ml of diisopropyl ether and, at room temperature, a mixture of 84.5 ml of ethylformate and 63.4 ml of ethyl acetate is added dropwise. The mixture is heated cautiously to 40°-44° C. After the vigorous evolution of hydrogen which starts during this, the mixture is stirred for a further 5 h with exclusion of moisture. The solid is filtered off with suction (96 g), the crude sodium salt of the formylacetic ester is dissolved in 350 ml of water, and 96 g (770 mmol) of methoxyacetamidine hydrochloride (cf. Chem. Abstr. 66, 37942×(1967)) dissolved in 350 ml of water are added. After the mixture has stood at room temperature for 3 days it is neutralized with hydrochloric acid, evaporated to dryness in vacuo and extracted by boiling several times with ethyl acetate. Evaporation of the solvent results in 62.5 g of product which is reacted further without further purification.

Workup

  1. additionis added dropwise
  2. temperatureThe mixture is heated cautiously to 40°-44° C
  3. filtrationThe solid is filtered off with suction (96 g)
  4. dissolutionthe crude sodium salt of the formylacetic ester is dissolved in 350 ml of water
  5. additionare added
  6. waitAfter the mixture has stood at room temperature for 3 days
  7. customevaporated to dryness in vacuo
  8. extractionextracted
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-06340155dc4b462aad3caf1b2cc76005
Source dataset
uspto-grants-1993_06
Patent number
US05215990

Reaction notes

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