1,1'-Carbonyldiimidazole → 3-[2-(4-Nitro-phenyl)-ethyl]-oxazolidin-2-one

HRID 241746Notes

Reaction equation

HRID 241746 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][CH2:25][CH2:26][OH:27])=[CH:18][CH:17]=1)([O-:15])=[O:14]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][O:27][C:6]2=[O:7])=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 227227442-[2-(4-Nitro-phenyl)-ethylamino]-ethanol

Product 1

HCID 107761683-[2-(4-Nitro-phenyl)-ethyl]-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

CDI (89 mmoles) is added to a solution of the compound obtained in Step A (44.5 mmoles) and DMAP (44.5 mmoles) in DCM (250 ml). After stirring for 4 hours at ambient temperature, the reaction mixture is diluted with 300 ml of DCM and then washed with 2M HCl solution (5×200 ml). The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness to yield the title product in the form of an orange solid, which is used directly in the next Step.

Workup

  1. washwashed with 2M HCl solution (5×200 ml)
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-fda4914ea9e44776990c417581b556d8
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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