Thionyl Chloride → HCID 90031616, compound

HRID 1048720Notes

Reaction equation

HRID 1048720 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH2:18][C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]2[C:9]=1[C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 90031842HCID 90031842, compound

Product 1

HCID 90031616HCID 90031616, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.238 g (0.949 mmol) of (3-(phenyl-ethynyl)imidazo[1,2-a]pyridin-2-yl) methanol were dissolved in 5 ml of dichloromethane with magnetic stirring and then 0.346 ml (4.75 mmol) of thionyl chloride were added. The mixture was stirred at r.t. for 2 h before being concentrated in vacuo. The residue was taken up into 20 ml of a mixture consisting of ethyl acetate and of a saturated NaHCO3 aqueous solution (1/1, v/v). After separation, the aqueous phase was extracted with 10 ml of ethyl acetate. The combined organic phases were washed with 10 ml of a saturated NaCl aqueous solution and then dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. 0.246 g (yield=96%) of 2-(chloromethyl)-3-(phenyl ethynyl)imidazo[1,2-a]pyridine were obtained as a brown solid. LC-MS: m/z=267 (MH+); UV purity at 254 nm=98%.

Workup

  1. stirringThe mixture was stirred at r.t. for 2 h
  2. concentrationbefore being concentrated in vacuo
  3. customAfter separation
  4. extractionthe aqueous phase was extracted with 10 ml of ethyl acetate
  5. washThe combined organic phases were washed with 10 ml of a saturated NaCl aqueous solution
  6. customdried on Na2SO4 which
  7. customwas then removed by filtration
  8. concentrationThe obtained filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c8f3980f72dd4e51afd3c79d54500e91
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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