Hydrogen Peroxide → N-(3,4-Dichlorophenyl)-N'-[5-(hexylsulfanyl)-1,3,4-thiadiazol-2-yl]urea

HRID 1729939Notes

Reaction equation

HRID 1729939 reaction equation
OO.[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][C:12]([NH:14][C:15]2[S:16][C:17]([S:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=O)=O)=[N:18][N:19]=2)=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10]>C(O)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][C:12]([NH:14][C:15]2[S:16][C:17]([S:20][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[N:18][N:19]=2)=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 21498388N-(3,4-Dichlorophenyl)-N'-[5-(hexane-1-sulfonyl)-1,3,4-thiadiazol-2-yl]urea

Product 1

HCID 18971675N-(3,4-Dichlorophenyl)-N'-[5-(hexylsulfanyl)-1,3,4-thiadiazol-2-yl]urea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6.0 g. (0.015 mole) of 1-(3,4-dichlorophenyl)-3-[5-(hexylthio)-1,3,4-thiadiazol-2-yl]urea (Example 18) was prepared in 30 ml. of glacial acetic acid. The mixture was heated to about 85°-90° C. and 4.08 g. (0.036 mole) of 30 percent hydrogen peroxide was added dropwise. After addition was complete, the temperature of the reaction mixture was maintained at about 85°-90° C. for an additional 1.5 hours. The reaction mixture was then cooled and poured onto ice. A precipitate formed which was filtered off and washed with water. The solid thus obtained was recrystallized from a mixture of ethyl acetate and normal hexane to yield product having a melting point of about 204°-206° C., and identified by elemental analyses and NMR spectrum as 1-(3,4-dichlorophenyl)-3-[5-(hexylsulfonyl)-1,3,4-thiadiazol-2-yl]urea.

Workup

  1. temperatureThe mixture was heated to about 85°-90° C.
  2. additionAfter addition
  3. temperaturethe temperature of the reaction mixture was maintained at about 85°-90° C. for an additional 1.5 hours
  4. temperatureThe reaction mixture was then cooled
  5. additionpoured onto ice
  6. customA precipitate formed which
  7. filtrationwas filtered off
  8. washwashed with water
  9. customThe solid thus obtained
  10. customwas recrystallized from a mixture of ethyl acetate and normal hexane
  11. customto yield product

Sources & evidence

ORD record
ord-76bc335f63174b42b863416a1f5f658e
Source dataset
uspto-grants-1976_11
Patent number
US03990879

Reaction notes

Loading…