Toluene → HCID 178443604, compound

HRID 1073469Notes

Reaction equation

HRID 1073469 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(C([N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)=C(O)C(CC)CC)#N.C([N:29]([CH2:32][CH3:33])CC)C.[C:34]1([CH3:40])[CH:39]=[CH:38]C=[CH:36][CH:35]=1>>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([C:40]([CH:34]([CH2:39][CH3:38])[CH2:35][CH3:36])=[C:33]([C:32]#[N:29])[C:26]2[N:25]=[CH:24][NH:23][N:22]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 70356430HCID 70356430, compound

Product 1

HCID 178443604HCID 178443604, compoundYield 68%

Procedure

0.5 g of 4-N,N'-dimethylaminopyridine and then 50 g (0.25 mol) of p-toluenesulfonyl chloride are added to a suspension of 50 g (0.24 mol) of 1-cyano-1-(1,2,4-triazol-1-yl)-3-ethyl-1-penten-2-ol in 300 ml of toluene. 50 ml (0.36 mol) of triethylamine are then added dropwise. Stirring is carried out for 40 hours at room temperature, the mixture is extracted by shaking with water, the organic phase is evaporated down and the product is allowed to crystallize out. Recrystallization from ethanol gives 60 g (68%) of 2-(4-methylphenylsulfonyl)-1-cyano-1-(1,2,4-triazolyl)-3-ethyl-1-pentene in the form of a Z/E isomer mixture. Mp. 78-87° C.

Workup

  1. extractionthe mixture is extracted
  2. stirringby shaking with water
  3. customthe organic phase is evaporated down
  4. customto crystallize out
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-74b4b4c2923b4e5f81660de70a6cf63c
Source dataset
uspto-grants-1990_11
Patent number
US04969950

Reaction notes

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