N-allyl-N-carbobenzyloxy-4-(4-pyridyl)-3,5-difluoraniline → (+/-)-5-Iodomethyl-3-[4-(4-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone

HRID 865366Notes

Reaction equation

HRID 865366 reaction equation
[CH2:1]([N:4]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:7]([F:18])[CH:6]=1)[CH:2]=[CH2:3].[I-:29].O1CCNC1=O>>[I:29][CH2:3][CH:2]1[O:20][C:19](=[O:21])[N:4]([C:5]2[CH:6]=[C:7]([F:18])[C:8]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)=[C:9]([F:11])[CH:10]=2)[CH2:1]1

Participants

3

Reactant 2

HCID 9999803N-allyl-N-carbobenzyloxy-4-(4-pyridyl)-3,5-difluoranilineHCID 21585223Oxazolidinone iodide

Product 1

HCID 10432033(+/-)-5-Iodomethyl-3-[4-(4-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone

Procedure

Following the general procedure of PREPARATION 5 and making non-critical variations but starting with N-allyl-N-carbobenzyloxy-4-(4-pyridyl)-3,5-difluoroaniline (PREPARATION 10, 241 mg, 0.634 mmol) is converted to the oxazolidinone iodide. The crude product is not purified further, NMR (CDCl3) δ 8.70, 7.44, 7.32, 4.85-4.73, 4.19, 3.80, 3.50, 3.40.

Workup

  1. customthe general procedure of PREPARATION 5
  2. customThe crude product is not purified further

Sources & evidence

ORD record
ord-8571cab36da441bc8a3fbc3eeb3fc084
Source dataset
uspto-grants-1996_10
Patent number
US05565571

Reaction notes

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