HCID 12831745, compound → HCID 178512704, compound

HRID 1660143Notes

Reaction equation

HRID 1660143 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].CS[C:17]1[NH:18][CH2:19][CH2:20][CH2:21][C:22]=1[N+:23]([O-:25])=[O:24]>C(O)C>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]2[NH:18][CH2:19][CH2:20][CH2:21][C:22]=2[N+:23]([O-:25])=[O:24])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 12831745HCID 12831745, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178512704HCID 178512704, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-guanidino-4-thiazolylmethylthio)ethylamine (0.8 g, 3.5 mmol) and 2-methylthio-3-nitro-1,4,5,6-tetrahydropyridine (0.5 g, 2.9 mmol) in ethanol (50 ml) was refluxed for 3 hours then left to stand at room temperature overnight. 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 twice from methanol/ether. Yield: 0.16 g, 15%. M.P. 211°-212.5° C.

Workup

  1. waitthen left
  2. customThe solvent was removed in vacuo
  3. customthe residue chromatographed on a silica-gel column
  4. washThe product was eluted with ethyl acetate/propan-2-ol (8:2)
  5. customrecrystallised twice from methanol/ether

Sources & evidence

ORD record
ord-6d8b39602ca74cc2b62d12ade3f34dac
Source dataset
uspto-grants-1981_12
Patent number
US04307104

Reaction notes

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