Sodium → HCID 178512706, compound

HRID 2198744Notes

Reaction equation

HRID 2198744 reaction equation
Cl.Cl.[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH2:16])[N:11]=1)[C:4]([NH2:6])=[NH:5].[Na].CS([C:21]1[NH:22][CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])=O>C(O)C>[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH:16][C:21]2[NH:22][CH:23]=[CH:24][C:25]=2[N+:26]([O-:28])=[O:27])[N:11]=1)[C:4]([NH2:6])=[NH:5]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 130595162-Methylsulphinyl-3-nitropyrroleHCID 178478806HCID 178478806, compound

Product 1

HCID 178512706HCID 178512706, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-(2-guanidino-4-thiazolylmethylthio)-ethylamine dihydrochloride (4 g, 0.013 mole) in ethanol (25 ml) was basified with a solution of sodium (0.65 g, 0.028 mole) in ethanol (20 ml). The mixture was filtered and the filtrate added to 2-methylsulphinyl-3-nitropyrrole (1.5 g, 0.0086 mole). The mixture was refluxed for 5 days, then the solvent was removed in vacuo and the residue chromatographed on a silica-gel column. The product was eluted with ethyl acetate/propan-2-ol (8:2) and recrystallised from methanol/acetone (6:4). Yield: 0.65 g, 22%. M.P. 195.5°-200° C.

Workup

  1. filtrationThe mixture was filtered
  2. temperatureThe mixture was refluxed for 5 days
  3. customthe solvent was removed in vacuo
  4. customthe residue chromatographed on a silica-gel column
  5. washThe product was eluted with ethyl acetate/propan-2-ol (8:2)
  6. customrecrystallised from methanol/acetone (6:4)

Sources & evidence

ORD record
ord-47ee38575082420f8e8ea6086eb95e7d
Source dataset
uspto-grants-1982_11
Patent number
US04359466

Reaction notes

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