Aniline → N'-(3-chloro-4-(2-oxo-3-oxazolidinyl)phenyl)-N-methyl-N-(2-propenyloxy)urea

HRID 903005Notes

Reaction equation

HRID 903005 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][O:13][C:12]1=[O:16].[H][H].[NH2:19][C:20]1C=CC=CC=1.[C:26](Cl)(Cl)=[O:27].[N-]=C=O.[O:33]1C[CH2:36][CH2:35][CH2:34]1>[Ni].C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:26](=[O:27])[N:19]([CH3:20])[O:33][CH2:34][CH:35]=[CH2:36])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][O:13][C:12]1=[O:16]

Participants

9

Reactant 6

HCID 6115AnilineHCID 6371PhosgeneHCID 8028Tetrahydrofuran2×HCID 105034IsocyanateHCID 233373183-(2-Chloro-4-nitrophenyl)-2-oxazolidinoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 23337321N'-(3-chloro-4-(2-oxo-3-oxazolidinyl)phenyl)-N-methyl-N-(2-propenyloxy)urea

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4.8 g of 1B was reduced with hydrogen in a Parr shaker (Raney nickel catalyst, tetrahydrofuran solvent, 50 p.s.i.g. hydrogen). A solution of the resulting aniline in ethyl acetate was treated with an excess of phosgene (5 hours at reflux). A solution of the resulting isocyanate in tetrahydrofuran was treated with 3.5 g of 3C (12 hours, room temperature). The resulting crude product was purified by silica gel chromatography to give 3, as a white solid, mp: 133°-135° C.

Workup

  1. customThe resulting crude product was purified by silica gel chromatography
  2. customto give 3

Sources & evidence

ORD record
ord-758e19832e8b46fc980e992dac68d235
Source dataset
uspto-grants-1980_10
Patent number
US04226612

Reaction notes

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