Sodium Methoxide → Sodium Sulfate

HRID 223282Notes

Reaction equation

HRID 223282 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[NH2:6][C:7]([NH:9][C:10]([NH2:12])=[NH:11])=[NH:8].C[O-].[Na+:15].NC(NC(N)=N)=N>CO>[S:1]([O-:5])([O-:4])(=[O:3])=[O:2].[Na+:15].[Na+:15].[NH2:8][C:7]([NH:9][C:10]([NH2:12])=[NH:11])=[NH:6]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 176517607CarbamimidamidomethanimidamideHCID 176518576Imidodicarbonimidic diamide sulfate

Product 2

HCID 24436Sodium SulfateHCID 176517607Carbamimidamidomethanimidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Biguanide was prepared fresh by refluxing anhydrous biguanide sulfate in a methanol solution of freshly prepared sodium methylate by the method of Slotta et al. (Slotta, K. H., Tschesche, R., Ber. Dtsch. Chem. Ges. 1929, B62, 1390-1398). The biguanide was used in solution as prepared for all of the reactions. Because sodium sulfate formed in the preparation of biguanide did not interfere with subsequent reactions, it was not necessary to separate it from the biguanide. Ethyl malonamate used in the preparation of Ib (see Example I below) was prepared as follows by methods of Galat and Marguery (Galat, A., J. Am. Chem. Soc. 1948, 70, 2596 and Marguery, M. F., Bull. Soc. Chem. France 1905, 33, 541; J. Recherces Centr. Nalt. Recherche Sci., Labs. Bellevue (Pairs) 1959, 47, 147), through Chem. Abstr. 1962, 56, 4744g.): Diethyl malonate was converted to the mono-potassium salt of the half-ester. The latter was converted to ethyl malonyl chloride, which in turn was reacted with anhydrous ammonia in ice-cold ether to form ethyl malonamate.

Workup

  1. customBiguanide was prepared fresh
  2. customas prepared for all of the reactions

Sources & evidence

ORD record
ord-437d4ade8bf34c9e91e8e4100fdb59e3
Source dataset
uspto-grants-1982_10
Patent number
US04352930

Reaction notes

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