Dichromate ion → HCID 19010355, compound

HRID 1741605Notes

Reaction equation

HRID 1741605 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[N:6][C:7]([C:14]2[NH:15][C:16](=[O:23])[C:17]([CH:20]([CH3:22])[CH3:21])([CH3:19])[N:18]=2)=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])[CH3:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:2]([C:4]1[CH:5]=[N:6][C:7]([C:14]2[NH:15][C:16](=[O:23])[C:17]([CH:20]([CH3:21])[CH3:22])([CH3:19])[N:18]=2)=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 24503Dichromate ionHCID 9813011pyridine TFAHCID 19010330HCID 19010330, compound

Product 1

HCID 19010355HCID 19010355, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.2 g of methyl 5-(1-hydroxyethyl)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate, 14.5 g of pyridinum dichromate and 1.99 g of pyridinium trifluoroacetate in 30 mL of methylene chloride is stirred at room temperature under nitrogen for 3 days. The reaction mixture is flash-chromatographed through florisil using methylene chloride as eluent, and the combined eluates are washed with water, dried, and concentrated in vacuo to a dark oil. Chromatography of this oil on silica gel using ether-hexane as eluant affords the desired product as a solid. Recrystallization of this solid from methylene chloride-hexane affords a white solid, mp 105°-108° C.

Workup

  1. customThe reaction mixture is flash-chromatographed through florisil
  2. washthe combined eluates are washed with water
  3. customdried
  4. concentrationconcentrated in vacuo to a dark oil

Sources & evidence

ORD record
ord-c833057ec9a7402b807cd34ec16c92a8
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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