Pyridine → HCID 54100544, compound

HRID 615066Notes

Reaction equation

HRID 615066 reaction equation
S(Cl)(Cl)=O.[N:5]1([CH:10](O)[CH:11]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[N:8]N=C1.[N:27]1C=CC=C[CH:28]=1>ClCCl>[N:5]1([CH:10]=[C:11]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[C:12]([CH3:13])([CH3:14])[CH3:15])[CH:9]=[N:8][CH:28]=[N:27]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20428854HCID 20428854, compound

Product 1

HCID 54100544HCID 54100544, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

With stirring, 100 ml of dichloromethane and 10 ml of thionyl chloride are cooled to -30° C. and then 17.5 g (0.05 mole) of 1-(1H-1,3,4-triazolyl)-2-(2,4-dichlorophenoxymethyl)-3,3-dimethylbutanol are added in portions. The reaction mixture is stirred for 2 hours and then a solution of 15 ml of pyridine in 30 ml of dichloromethane is added dropwise and the mixture is stirred for about 12 hours at room temperature. The clear solution is concentrated in vacuo and, after addition of ice, the residue is made alkaline with sodium carbonate and extracted with diethyl ether. The combined extracts are dried over sodium sulfate, filtered and concentrated. The yellowish oily residue is purified by column chromatography over silica gel with ethyl acetate as eluant. Yield: 75% of theory.

Workup

  1. stirringThe reaction mixture is stirred for 2 hours
  2. stirringthe mixture is stirred for about 12 hours at room temperature
  3. concentrationThe clear solution is concentrated in vacuo
  4. additionafter addition of ice
  5. extractionextracted with diethyl ether
  6. dry with materialThe combined extracts are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe yellowish oily residue is purified by column chromatography over silica gel with ethyl acetate as eluant

Sources & evidence

ORD record
ord-f53b659eb6f646d58deec1704eca3428
Source dataset
uspto-grants-1985_02
Patent number
US04497647

Reaction notes

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