Sodium ethoxide → HCID 178512693, compound

HRID 1758738Notes

Reaction equation

HRID 1758738 reaction equation
Cl.C(=N)([O:4]CC)C.[O-]CC.[Na+].[Na].[NH:13]([C:17]1[S:18][CH:19]=[C:20]([C:22](NN)=[O:23])[N:21]=1)[C:14]([NH2:16])=[NH:15]>C(O)C>[NH:13]([C:17]1[S:18][CH:19]=[C:20]([C:22]([OH:23])=[O:4])[N:21]=1)[C:14]([NH2:16])=[NH:15]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 5360545SodiumHCID 178512692HCID 178512692, compound

Product 1

HCID 178512693HCID 178512693, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

37.1 g (0.3 mol) of ethyl acetimidate hydrochloride was dissolved in 200 ml absolute ethanol. A solution of sodium ethoxide (6.9 g (0.3 mol) sodium in 300 ml absolute ethanol) was added. The resulting precipitate of sodium chloride was removed by filtration and to the clear filtrate was added 20.0 g (0.1 mol) of 2-guanidino-4-thiazole carboxylic acid hydrazide. The slurry was stirred at 25° for 60 hours, during which time complete dissolution occurred. The clear, pale orange solution was concentrated in vacuo to a soft solid which was triturated in 10:1 ethyl acetate-ethanol to give 24.0 g (88%) of crude 2-guanidino-4-thiazole carboxylic acid 2-acetiminohydrazide, with a broad melting point, 150° to 178° (dec.).

Workup

  1. customThe resulting precipitate of sodium chloride was removed by filtration and to the clear filtrate
  2. concentrationThe clear, pale orange solution was concentrated in vacuo to a soft solid which
  3. customwas triturated in 10:1 ethyl acetate-ethanol

Sources & evidence

ORD record
ord-94f44944e8d1463bb7dc6847021b156f
Source dataset
uspto-grants-1983_02
Patent number
US04374843

Reaction notes

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