Hydrochloric Acid → HCID 89601219, compound

HRID 530242Notes

Reaction equation

HRID 530242 reaction equation
O[C:2]1([C:12]#[N:13])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].S(Cl)(Cl)=O.Cl>N1C=CC=CC=1>[CH3:8][C:6]1([CH3:9])[CH2:5][CH2:4][C:3]([CH3:10])([CH3:11])[C:2]([C:12]#[N:13])=[CH:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 89601462HCID 89601462, compound

Product 1

HCID 89601219HCID 89601219, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of the product of Example 10e (2.22 g, 12.3 mmol) in pyridine (40 mL) was added thionyl chloride (4.4 mL, 61.3 mmol) and the reaction was stirred at room temperature for 2 hours. The reaction was acidified with 5 N hydrochloric acid to pH=1, then it was poured into ice-water (20 mL). The aqueous mixture was extracted with ethyl acetate (20 ml×3) and the organic phase washed with water (20 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound as a colorless oil (600 mg, Yield: 30%). 1H NMR (400 MHz, CDCl3) δ 6.23 (s, 1H), 1.56 (t, J=2.8 Hz, 2H), 1.56-1.43 (m, 4H), 1.16 (s, 6H), 1.03 (s, 6H) ppm.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (20 ml×3)
  2. washthe organic phase washed with water (20 mL), brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfc06d9bf2db402298c11a7f0d4b5b7a
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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