Phosphorus oxide (P4O10) → HCID 66914929, compound

HRID 880505Notes

Reaction equation

HRID 880505 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CO[CH:17]([O:32]C)[CH2:18][NH:19][C:20](=O)[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([F:30])[CH:22]=1>CS(O)(=O)=O>[F:30][C:23]1[CH:22]=[C:21]([C:20]2[O:32][CH:17]=[CH:18][N:19]=2)[CH:26]=[CH:25][C:24]=1[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 55103942N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamide

Product 1

HCID 66914929HCID 66914929, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
145 °C

Procedure

Phosphorous pentoxide (4.14 g, 29.41 mmol) was added portion-wise to a solution of N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamide (2.0 g, 7.35 mmol) in methane sulphonic acid (3 mL) at 0° C. over a period of 30 min. The mixture was heated to 145° C. for 5 h. The reaction mixture was allowed to cool to ambient temperature and quenched with crushed ice and then extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate and concentrated to afford the crude residue. Purification by flash chromatography with silica (60-120 mesh) using 15% ethyl acetate-petroleum ether as eluent to afforded 2-(3-fluoro-4-nitrophenyl)oxazole (500 mg, 33%) as a white solid.

Workup

  1. temperatureto cool to ambient temperature
  2. customquenched with crushed ice
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford the crude residue
  8. customPurification by flash chromatography with silica (60-120 mesh)

Sources & evidence

ORD record
ord-0c63fc95d3ba461d8998858a69ad7d44
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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