Pyridine → HCID 15869092, compound

HRID 1003146Notes

Reaction equation

HRID 1003146 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].N1C=CC=CC=1.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>C1COCC1.O>[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 15869092HCID 15869092, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-cyano-6-hydroxybenzothiazole (2.1 g, 12.5 mmol) in 30 mL of dry THF under inert atmosphere was treated with pyridine (2.0 g, 25 mmol) followed by pivaloyl chloride (1.95 g, 16.2 mmol). This reaction was stirred 15 h at room temperature. The reaction mixture was then diluted with 100 mL of distilled water, and this solution was extracted with ethyl acetate (4×50 mL). The combined organics were washed with aqueous sodium bicarbonate (2×100 mL) and distilled water (1×100 mL), then dried over Na2SO4 and concentrated under reduced pressure to afford 3.0 g of a thick oil. This material was chromatographed on silica gel and 1.8 g of the product was eluted with 10% ethyl acetate/hexanes. 1H NMR (CDCl3): δ 1.39 (s, 9H); 7.34-7.38 (m, 1H); 7.74-7.75 (d, 1H) ; 8.20-8.23 (d, 1H).

Workup

  1. extractionthis solution was extracted with ethyl acetate (4×50 mL)
  2. washThe combined organics were washed with aqueous sodium bicarbonate (2×100 mL)
  3. distillationdistilled water (1×100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-924151fd63164ed0aea41915ab73ed2b
Source dataset
uspto-grants-2000_04
Patent number
US06045991

Reaction notes

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