Pyridine → 2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carbonyl chloride

HRID 2278931Notes

Reaction equation

HRID 2278931 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[O:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:7][CH2:6]1.N1C=CC=CC=1>C(Cl)Cl>[O:16]=[C:12]1[N:11]([CH:8]2[CH2:9][CH2:10][O:5][CH2:6][CH2:7]2)[CH2:15][CH2:14][N:13]1[C:1]([Cl:4])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 904259751-(Oxan-4-yl)imidazolidin-2-one

Product 1

HCID 904274552-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0° C. solution of phosgene (20% in toluene, 0.267 mL, 0.506 mmol) in DCM (5 mL) was treated slowly drop-wise with a solution of Example B1 (0.086 g, 0.505 mmol) and pyridine (0.082 mL, 1.011 mmol) in DCM (3 mL). The mixture was warmed to RT, stirred for 1 hour, then concentrated to dryness to afford 2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carbonyl chloride as an off-white solid. The material was carried on to the next step assuming 100% yield (118 mg). MS (ESI) m/z: 304.1 (M+H+) (for material quenched into benzylamine).

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dc18d9990823469cba3b9ed33855c231
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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