Sodium Chloride → HCID 178512693, compound

HRID 280737Notes

Reaction equation

HRID 280737 reaction equation
Cl.C(=N)([O:4]CC)C.[O-]CC.[Na+].[Na].[Cl-].[Na+].[NH:15]([C:19]1[S:20][CH:21]=[C:22]([C:24](NN)=[O:25])[N:23]=1)[C:16]([NH2:18])=[NH:17]>C(O)C>[NH:15]([C:19]1[S:20][CH:21]=[C:22]([C:24]([OH:25])=[O:4])[N:23]=1)[C:16]([NH2:18])=[NH:17]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 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. customwas 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-419e02562aad4a549111a57ec1f5b8ee
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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