Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178482521, compound

HRID 1758595Notes

Reaction equation

HRID 1758595 reaction equation
CO[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:25]([NH2:32])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:3]1[C:7]([NH:32][CH3:25])=[N:6][S:5](=[O:11])(=[O:10])[N:4]=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 178482521HCID 178482521, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a well stirred suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.5 g; 14.0 mmoles) in 250 ml of dry methanol that had been cooled to 2° in an ice-water bath was added dropwise over a period of 25 minutes a solution of 2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 3.42 g; 14.0 mmoles) in 25 ml of methanol. After stirring at 2° for 20 minutes, anhydrous methylamine was bubbled into the solution for 6 minutes and stirring was continued at ambient temperature for 30 minutes. The reaction mixture was evaporated under reduced pressure and the residue was placed on 50 g of silica gel and chromatographed by gradient elution using methylene chloride-methanol. The appropriate fractions were combined to give 3.2 g of the title compound. Additional purification of the product using column chromatography gave an analytical sample of the title compound as an amorphous solid, mp 98°-110°. The NMR spectrum (100 MHz) in d6 dimethyl sulfoxide gave the following resonances δ: 7.46 (s, 1H); 3.70 (s, 2H); 2.53 (t, 2H); 2.86 (s, 3H); 2.72 (t, 2H); 2.15 (s, 3H).

Workup

  1. temperaturehad been cooled to 2° in an ice-water bath
  2. stirringAfter stirring at 2° for 20 minutes
  3. customanhydrous methylamine was bubbled into the solution for 6 minutes
  4. stirringstirring
  5. customThe reaction mixture was evaporated under reduced pressure
  6. customchromatographed by gradient elution

Sources & evidence

ORD record
ord-85d8bb312489427fb3d928cf12214f76
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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