Pyridine → 3-Nitro-5-oxazol-2-yl-benzoic acid methyl ester

HRID 1664209Notes

Reaction equation

HRID 1664209 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:28][O:29][C:30](=[O:46])[C:31]1[CH:42]=[C:41]([N+:43]([O-:45])=[O:44])[CH:40]=[C:33]([C:34]([NH:36][CH2:37][CH:38]=[O:39])=O)[CH:32]=1.N1C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH3:28][O:29][C:30](=[O:46])[C:31]1[CH:32]=[C:33]([C:34]2[O:39][CH:38]=[CH:37][N:36]=2)[CH:40]=[C:41]([N+:43]([O-:45])=[O:44])[CH:42]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 866265795-Nitro-N-(2-oxo-ethyl)-isophthalamic acid methyl ester

Product 1

HCID 674407033-Nitro-5-oxazol-2-yl-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of hexachloroethane (42.7 g, 180 mmol) and 47.2 g of triphenylphosphine (180 mmol) in 1 l of acetonitrile is stirred for 20 minutes. A solution of 24 g (90.2 mmol) of 5-nitro-N-(2-oxo-ethyl)-isophthalamic acid methyl ester in 400 ml of acetonitrile is added, followed by 25.8 ml (361 mmol) of pyridine. After 18 h at rt, the mixture is diluted with 500 ml of ethyl acetate and washed with brine. The organic phase is dried over sodium sulfate and concentrated, and the residue is purified by chromatography on silica gel (EtOAc/hexane 1:3) to yield the product in the form of colorless crystals.

Workup

  1. waitAfter 18 h at rt
  2. washwashed with brine
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is purified by chromatography on silica gel (EtOAc/hexane 1:3)
  6. customto yield the product in the form of colorless crystals

Sources & evidence

ORD record
ord-75a361b00cc941c99cc5a638610dd1cf
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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