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Phosphorus oxychloride → 3-(2-Chloroethyl)imidazo[1,5-a]pyrazine

HRID 566250
Notes
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Reaction equation

HRID 566250 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=O)[CH2:10][CH2:11][Cl:12].P(Cl)(Cl)(Cl)=O>ClCCl>[Cl:12][CH2:11][CH2:10][C:9]1[N:1]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]2=[CH:7][N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21265851N-(2-pyrazinylmethyl)-3-chloropropionamide

Product 1

HCID 212658743-(2-Chloroethyl)imidazo[1,5-a]pyrazineYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-pyrazinylmethyl)-3-chloropropionamide (4.52 g) in dichloromethane (30 ml) was added phosphorus oxychloride (1.29 g) under ice cooling. The mixture was stirred for 3 days at room temperature. The mixture was concentrated, and the residue was poured into ice water (400 ml), followed by neutralization with sodium carbonate. The reaction mixture was subjected to salting out with sodium chloride, and extracted with ethyl acetate-THF (1:1, 150 ml×3). The organic layers were combined and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to flash column chromatography [carrier: silica gel, 100 g, developing solvent: ethyl acetate→ethyl acetate-ethanol (9:1)]. The eluate was concentrated and residual solid was washed with diethylether to give the title compound (3.07 g) as colorless solid product.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was poured into ice water (400 ml)
  3. extractionextracted with ethyl acetate-THF (1:1, 150 ml×3)
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. concentrationThe eluate was concentrated
  7. washresidual solid was washed with diethylether

Sources & evidence

ORD record
ord-b88d7951211d4d7f9dcd0c0bec763463
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06174877B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes