1,1-Bis(methylthio)-2-nitroethylene → HCID 178503825, compound

HRID 2050154Notes

Reaction equation

HRID 2050154 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].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[CH3:29][S:30][C:31](SC)=[CH:32][N+:33]([O-:35])=[O:34]>C(O)(C)C>[N+:33]([CH:32]=[C:31]([S:30][CH3:29])[NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=1)([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178503825HCID 178503825, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 20.0 g; 66.0 mmoles) [prepared according to the procedure described in South Africa Pat. No. 78/2129] and 1,1-bis(methylthio)-2-nitroethylene [prepared according to the procedure described in Chem. Ber., 100, 591 (1967) or Acta Chem. Scand., 21 2797 (1967)] (10.9 g; 66.0 mmoles) in isopropanol (600 ml) was stirred at ambient temperature under a positive pressure of nitrogen for 2 hours, at reflux temperature for 1 hour and then at ambient temperature for 54 hours. The reaction mixture was cooled and filtered to give 15.8 g of 1-nitro-2-methylthio-2-{2-[(2-guanidinothiazol-4-yl)methylthio]ethylamino}ethylene as a yellow solid, mp 151°-156°, which was used without further purification in Step B below.

Workup

  1. custom66.0 mmoles) [prepared
  2. temperatureat reflux temperature for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b40cf9476e364419b11a74c464f1cf9e
Source dataset
uspto-grants-1980_04
Patent number
US04200578

Reaction notes

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