Ethoxalyl chloride → HCID 67028744, compound

HRID 455133Notes

Reaction equation

HRID 455133 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18](=[N:20][OH:21])[NH2:19])=[CH:4][CH:3]=1.Cl[C:23](=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[N:19]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[O:21][N:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 866551272-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N'-hydroxyacetimidamide

Product 1

HCID 67028744HCID 67028744, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-40 °C

Procedure

To a suspension of 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N′-hydroxyacetimidamide (83.3 mmol, 25.0 g) in dry CHCl3 (600 mL) was cooled to −40° C. in an ice/EtOH bath under N2 atmosphere, Py. (100.0 mmol, 8.1 mL) was added in one portion, and followed by slowly adding ethyl 2-chloro-2-oxoacetate (166.6 mmol, 18.6 mL). After that, the reaction mixture was allowed to slowly rise up to r.t., and kept stirring for 1.0 H, D, then heated to 80 C for another 2 hs. The reaction mixture was cooled to r.t. and filtered, and the filtrate was evaporated under reduced pressure to give the brown residue, which was applied to C.C.eluted by petroleum/acetone (4:1, 2:1, 1:1, and 0:1). The acetone portion was concentrated in vacuo to give the solid, which was washed with acetone for 3 times, to obtain the product, 18.0 g (58.0%), as a white solid. m/e+=383 (M+H+).

Workup

  1. addition(100.0 mmol, 8.1 mL) was added in one portion
  2. customto slowly rise up to r.t.
  3. temperatureheated to 80 C for another 2 hs
  4. temperatureThe reaction mixture was cooled to r.t.
  5. filtrationfiltered
  6. customthe filtrate was evaporated under reduced pressure
  7. customto give the brown residue, which
  8. concentrationThe acetone portion was concentrated in vacuo
  9. customto give the solid, which
  10. washwas washed with acetone for 3 times
  11. customto obtain the product, 18.0 g (58.0%)

Sources & evidence

ORD record
ord-1b01db47e44047ec9440c6377ed82d08
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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