Iodine → Bis[1-(4-chlorophenyl)-4-(pyrid-3-yl)2,3-diazabutadien-1-yl]disulfide

HRID 330590Notes

Reaction equation

HRID 330590 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:13][N:14]=2)=[CH:6][CH:5]=1.II>CC(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([S:11][S:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)=[N:14][N:13]=[CH:12][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:14][N:13]=[CH:12][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 157083633-[5-(4-Chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl]pyridine

Product 1

HCID 53981879Bis[1-(4-chlorophenyl)-4-(pyrid-3-yl)2,3-diazabutadien-1-yl]disulfide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.6 g of powdered potassium hydroxide are added to a solution, cooled to 0° C., of 15 g of the 2-(4-chlorophenyl)-5-(pyrid-3-yl)-4,5-dihydro-1,3,4-thiadiazole prepared according to Example 1a) in 80 ml of acetone. After stirring for ca. 5 minutes at 0°-5° C., 6.9 g of iodine are added in portions and the exothermic reaction is kept at about 0°-5° C. by cooling with ice. The batch is subsequently stirred for 4 hours at ca. 0° C. The precipitated product is isolated by filtration and washed with a small amount of acetone. The crude product is taken up in a 1:3 mixture of tetrahyrofuran/ethyl acetate and the solution is washed once with water and twice with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated by evaporation. The title compound of formula ##STR20## so obtained has a melting point of 143°-145° C. (compound 21).

Workup

  1. customprepared
  2. customthe exothermic reaction
  3. customis kept at about 0°-5° C.
  4. temperatureby cooling with ice
  5. stirringThe batch is subsequently stirred for 4 hours at ca. 0° C
  6. customThe precipitated product is isolated by filtration
  7. washwashed with a small amount of acetone
  8. additionThe crude product is taken up in a 1:3 mixture of tetrahyrofuran/ethyl acetate
  9. washthe solution is washed once with water and twice with a saturated solution of sodium chloride
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f972ae0b73d5405a802afb4d13cd9ccc
Source dataset
uspto-grants-1990_01
Patent number
US04897485

Reaction notes

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