Water → HCID 20043724, compound

HRID 1761942Notes

Reaction equation

HRID 1761942 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)(O)[CH:9]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH3:10])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:9]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH3:10])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 12875945HCID 12875945, compound

Product 1

HCID 20043724HCID 20043724, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,1-bis(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)propan-1-ol (2.0 g) from Example 3xi was dissolved in dry toluene (40 ml), and a catalytic amount of p-toluene sulphonic acid added. The mixture was refluxed in a round bottom flask fitted with a soxhlet extractor filled with molecular sieves (4A) and condenser. Reflux was continued until there was no starting material remaining on tlc. The mixture was poured into water and extracted, washed with water (3X) then dried over anhydrous magnesium sulphate and evaporated on a rotary evaporator. The product was purified by chromatography on silica gel eluted with CH2Cl2 /ethylacetate (3:2). 1,1-bis(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-1-ene was obtained as a white solid (1.0 g) by recrystallisation from hexane.

Workup

  1. temperatureThe mixture was refluxed in a round bottom flask
  2. customfitted with a soxhlet extractor
  3. temperatureReflux
  4. extractionextracted
  5. washwashed with water (3X)
  6. dry with materialthen dried over anhydrous magnesium sulphate
  7. customevaporated on a rotary evaporator
  8. customThe product was purified by chromatography on silica gel
  9. washeluted with CH2Cl2 /ethylacetate (3:2)

Sources & evidence

ORD record
ord-c545926d5ea24939bda34a9f356946b2
Source dataset
uspto-grants-1989_05
Patent number
US04829074

Reaction notes

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