Tetrafluoro-m-phenylenediamine dihydrochloride → 4-methoxy-N-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]-1,1-dioxo-1,2,5-thiadiazol-3-amine

HRID 2418019Notes

Reaction equation

HRID 2418019 reaction equation
[CH3:1][O:2][C:3]1[C:7](OC)=[N:6][S:5](=[O:11])(=[O:10])[N:4]=1.[CH3:12][C:13]1[NH:17][CH:16]=[N:15][C:14]=1[CH2:18][S:19][CH2:20][CH2:21][NH2:22].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CO>[CH3:12][C:13]1[NH:17][CH:16]=[N:15][C:14]=1[CH2:18][S:19][CH2:20][CH2:21][NH:22][C:7]1[C:3]([O:2][CH3:1])=[N:4][S:5](=[O:11])(=[O:10])[N:6]=1

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxide

Product 1

HCID 1784943354-methoxy-N-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]-1,1-dioxo-1,2,5-thiadiazol-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a well stirred suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.0 g; 11.2 mmoles) [prepared according to the procedure described in J. Org. Chem., 40, 2743 (1975)] in 200 ml of methanol at ambient temperature was added a solution of 2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 2.73 g; 11.2 mmoles) [prepared according to Belgian Pat. No. 779,775] in 25 ml of methanol. After stirring for 30 minutes, a methanolic solution of the title compound was produced. The TLC (Silica/CH2Cl2 :CH3OH (90:10)] gave Rf=0.44.

Workup

  1. customprepared
  2. custom11.2 mmoles) [prepared
  3. stirringAfter stirring for 30 minutes

Sources & evidence

ORD record
ord-ce422d09be944c4599342b78eae6ce8b
Source dataset
uspto-grants-1984_09
Patent number
US04471122

Reaction notes

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