2-Methyl-2-thiopseudourea sulfate → HCID 178513174, compound

HRID 280736Notes

Reaction equation

HRID 280736 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]([NH:12][NH2:13])=[O:11])[N:9]=1)[C:2]([NH2:4])=[NH:3].S(O)(O)(=O)=O.CS[C:21](=[NH:23])[NH2:22]>CS(C)=O>[C:21]([NH:13][NH:12][C:10]([C:8]1[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=1)=[O:11])(=[NH:22])[NH2:23]

Participants

4

Reactant 2

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 178512692HCID 178512692, compound

Product 1

HCID 178513174HCID 178513174, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

17.9 g (0.089 mol) of 2 guanidino-4-thiazole carboxylic acid hydrazide was combined with 24.9 g of 2-methyl-2-thiopseudourea sulfate (0.089 mol) and heated rapidly to reflux in 125 ml dimethylsulfoxide. The reactants dissolved and within 5 minutes reflux a heavy precipitate formed. Reflux was continued for a total of 30 minutes. The reaction was cooled and the resulting heavy precipitate was isolated by filtration and washed with a small portion of dimethylsulfoxide followed by washing with isopropyl alcohol and ether. The resulting solid was dried in vacuo to give 34.6 g of 2-guanidino-4-thiazole carboxylic acid 2-amidinohydrazide containing some occluded dimethylsulfoxide.

Workup

  1. temperatureheated rapidly
  2. dissolutionThe reactants dissolved and within 5 minutes
  3. temperaturereflux a heavy precipitate
  4. customformed
  5. temperatureReflux
  6. customwas continued for a total of 30 minutes
  7. temperatureThe reaction was cooled
  8. customthe resulting heavy precipitate was isolated by filtration
  9. washwashed with a small portion of dimethylsulfoxide
  10. washby washing with isopropyl alcohol and ether
  11. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-e5aab5552e954996b14d5deb665ad63d
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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