Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178482519, compound

HRID 1980728Notes

Reaction equation

HRID 1980728 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH2:11])[N:6]=1.C1(N)C(F)=C(F)C(F)=[C:14]([NH2:21])C=1F.Cl.Cl.CO[C:28]1[C:32](OC)=[N:31][S:30](=[O:36])(=[O:35])[N:29]=1>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:28]2[C:32]([NH:21][CH3:14])=[N:31][S:30](=[O:36])(=[O:35])[N:29]=2)[N:6]=1

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 129234084-{[(2-Aminoethyl)sulfanyl]methyl}-1,3-thiazol-2-amine

Product 1

HCID 178482519HCID 178482519, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-[(2-aminothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 3.0 g; 11.4 mmoles) [prepared in Step A] in 25 ml of methanol was added dropwise over 1.5 hours to a cold (5°), stirred, partial suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.03 g; 11.4 mmoles) in 55 ml of methanol. After 1.5 hours, anhydrous methylamine was bubbled into the solution for 30 minutes and stirred at 5° for 19 hours. The reaction mixture was evaporated under reduced pressure and the residue placed on 400 g of silica gel and chromatographed using acetone-methylene chloride (7:3). The appropriate fractions were combined and evaporated to give product. Recrystallization from 95% ethanol yielded the title compound, mp 200°-201°.

Workup

  1. additionwas added dropwise over 1.5 hours to a cold (5°)
  2. customanhydrous methylamine was bubbled into the solution for 30 minutes
  3. stirringstirred at 5° for 19 hours
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customchromatographed
  6. customevaporated
  7. customto give product
  8. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-3d91f81b3e5f46e5a4a1197690535632
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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