Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178457004, compound

HRID 1758617Notes

Reaction equation

HRID 1758617 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].[C:15]1([NH2:26])[C:20](F)=[C:19](F)C(F)=C(N)C=1F.Cl.Cl.CO[C:31]1[C:35](OC)=[N:34][S:33](=[O:39])(=[O:38])[N:32]=1.C(N)C#C>CO>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:31]2[C:35]([NH:26][CH2:15][C:20]#[CH:19])=[N:34][S:33](=[O:39])(=[O:38])[N:32]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

6

Reactant 4

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 239041PropargylamineHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178457004HCID 178457004, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 3.42 g; 11.2 mmoles) in 25 ml of methanol was added to a well stirred cold (8°) suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.0 g; 11.2 mmoles) in 200 ml of methanol. After 15 minutes at 8°-10°, the solution was cooled to 1° in an ice-bath and a solution of 6.0 ml 2-propynylamine in 15 ml of methanol was added. The ice-bath was removed and stirring was continued for 15 minutes. The reaction mixture was evaporated under reduced pressure and the residue placed on 50 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. Two of the fractions yielded crystalline product (1.74 g) from methanol. The product was dissolved in hot methanol, filtered through Celite, cooled and filtered to yield the title compound, mp 176°-178°.

Workup

  1. temperaturethe solution was cooled to 1° in an ice-bath
  2. customThe ice-bath was removed
  3. waitwas continued for 15 minutes
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customchromatographed
  6. washa gradient elution of methylene chloride-methanol

Sources & evidence

ORD record
ord-70acc0546fbb42cfb94118d17047b90f
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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