4-Hydroxymethylpyridine → HCID 59013789, compound

HRID 907566Notes

Reaction equation

HRID 907566 reaction equation
[Cl:1][C:2]1[C:6](Cl)=[N:5][S:4][N:3]=1.[N:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C.O.Cl>[Cl:1][C:2]1[C:6]([O:15][CH2:14][C:11]2[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=2)=[N:5][S:4][N:3]=1

Participants

7

Reactant 3

HCID 114724-HydroxymethylpyridineHCID 798043,4-Dichloro-1,2,5-thiadiazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 59013789HCID 59013789, compoundYield 37.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

3,4-Dichloro-1,2,5-thiadiazole (2.00 mL, 21.3 mmol) was dissolved in 70 mL of t-butanol along with 4-pyridine methanol (1.05 g, 9.62 mmol). 30 mL of 1.0 M potassium t-butoxide (30 mmol) was added and the reaction was stirred at room temperature overnight. The reaction was diluted with 100 mL of water and neutralized with 1.0 M HCl. The product was extracted 3 times with 100 mL portions of ethyl acetate. The combined organic fractions were dried with magnesium sulfate and concentrated under vacuum. The residue was purified by flash chromatography with a 2:1 solution of hexanes in ethyl acetate, affording 4-(4-chloro-[1,2,5]thiadiazol-3-yloxymethyl)-pyridine (821 mg) as an off-white solid.

Workup

  1. extractionThe product was extracted 3 times with 100 mL portions of ethyl acetate
  2. dry with materialThe combined organic fractions were dried with magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography with a 2:1 solution of hexanes in ethyl acetate

Sources & evidence

ORD record
ord-b98ea9bf76bb4dd9b06d50a12f0ed9b4
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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