1-Butanol → HCID 23043296, compound

HRID 1721923Notes

Reaction equation

HRID 1721923 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[C:4]([O:16][CH:17]([F:19])[F:18])[CH:3]=1.C(O)CCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:36][CH2:37][CH:38]([OH:41])[CH2:39]O>C1(C)C=CC=CC=1>[F:18][CH:17]([F:19])[O:16][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[C:8]1([CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[O:41][CH:38]([CH2:37][Cl:36])[CH2:39][O:15]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acid2×HCID 72903-Chloro-1,2-propanediolHCID 23043297HCID 23043297, compound

Product 1

HCID 23043296HCID 23043296, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

14.2 parts of 1-(4-chloro-2-difluoromethoxyphenyl)-2-(1H-1,2,4-triazolyl)ethan-1-one and 100 ml of n-butanol in 450 ml of abs. toluene are heated in the presence of 9.4 parts of p-toluenesulfonic acid for 5 hours under reflux, while removing the water of reaction with a water separator. After cooling to 60° C., 33 parts of 3-chloro-1,2-propanediol and a further 18 parts of p-toluenesulfonic acid are added and the batch is refluxed for 80 hours while removing the water of reaction with a water separator. The reaction mixture is cooled to room temperature, washed twice with saturated aqueous sodium carbonate solution and with 2×200 ml of water, dried over sodium sulfate and filtered. The solvent is removed in a rotary evaporator and the oily residue is chromatographed through a 50 cm column of silica gel with a 1:1 mixture of methylene chloride/diethyl ether as eluant. The solvent mixture is removed by evaporation, affording the title compound in the form of a pale yellow oil with a refractive index nD22 : 1.5336.

Workup

  1. temperatureunder reflux
  2. customwhile removing
  3. customthe water of reaction with a water separator
  4. temperaturethe batch is refluxed for 80 hours
  5. customwhile removing
  6. customthe water of reaction with a water separator
  7. temperatureThe reaction mixture is cooled to room temperature
  8. washwashed twice with saturated aqueous sodium carbonate solution and with 2×200 ml of water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customThe solvent is removed in a rotary evaporator
  12. customthe oily residue is chromatographed through a 50 cm column of silica gel with a 1:1 mixture of methylene chloride/diethyl ether as eluant
  13. customThe solvent mixture is removed by evaporation

Sources & evidence

ORD record
ord-8a963bbcbf1a4d6f8b1bb1bb8206e21d
Source dataset
uspto-grants-1989_08
Patent number
US04853399

Reaction notes

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