Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178433672, compound

HRID 1758596Notes

Reaction equation

HRID 1758596 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:16](OC)=[N:15][S:14](=[O:20])(=[O:19])[N:13]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.CC1NC=NC=1CSCCN.[NH:46]([C:50]1[S:51][CH:52]=[C:53]([CH2:55][S:56][CH2:57][CH2:58][NH2:59])[N:54]=1)[C:47]([NH2:49])=[NH:48]>CO>[NH:46]([C:50]1[S:51][CH:52]=[C:53]([CH2:55][S:56][CH2:57][CH2:58][NH:59][C:16]2[C:12]([NH:11][CH2:10][CH2:9][S:8][CH2:7][C:3]3[N:4]=[CH:5][NH:6][C:2]=3[CH3:1])=[N:13][S:14](=[O:20])(=[O:19])[N:15]=2)[N:54]=1)[C:47]([NH2:49])=[NH:48]

Participants

6

Reactant 4

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride2×HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 1784943354-methoxy-N-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]-1,1-dioxo-1,2,5-thiadiazol-3-amineHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178433672HCID 178433672, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a well stirred solution at -10° of 3-{2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethylamino}-4-methoxy-1,2,5-thiadiazole 1,1-dioxide [prepared from the dihydrochloride of 2-{(5-methyl-1H-imidazol-4-yl)methylthio}ethylamine (2.73 g; 11.2 mmole) by the procedure of Step A of Example 1] was rapidly added a solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 3.41 g; 11.2 mmoles) [prepared according to the procedure described in South African Pat. No. 78/2129] in 35 ml of methanol. After stirring at -10° for 30 minutes, the solution was allowed to warm to ambient temperature. The reaction mixture was evaporated under reduced pressure and the residue was placed on 45 g of silica gel and chromatographed using 1 liter of methylene chloride-methanol (4:1). The appropriate fractions were combined and evaporated, and the residue (5.82 g) was placed on 80 g of aluminum oxide and chromatographed using a gradient elution of ethyl acetate-methanol. The appropriate fractions were combined, filtered through Celite and evaporated under high vacuum to yield the title compound (2.5 g) as an amorphous solid containing approximately 2/3 mole of ethyl acetate, as ascertained by the NMR spectrum (100 MHz) in d6 dimethyl sulfoxide.

Workup

  1. custom11.2 mmoles) [prepared
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customchromatographed
  4. customevaporated
  5. customchromatographed
  6. washa gradient elution of ethyl acetate-methanol
  7. filtrationfiltered through Celite
  8. customevaporated under high vacuum

Sources & evidence

ORD record
ord-ae6ddda734724b7e9f771443931fc7d4
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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