Vinylene carbonate → 2-(4-Nitrobenzyl)oxazole

HRID 1508861Notes

Reaction equation

HRID 1508861 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].O1[CH:18]=[CH:17]OC1=O.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][CH:17]=[CH:18][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 13385Vinylene carbonateHCID 2336132-(4-Nitrophenyl)acetamideHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 901105832-(4-Nitrobenzyl)oxazoleYield 25%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-nitrophenyl)acetamide (1.0 g, 5.55 mmol), 1,3-dioxol-2-one (0.955 g, 11.10 mmol), and Eaton's Reagent (9.9 g, 34.97 mmol) was heated to 100° C. overnight under a nitrogen atmosphere. After this time, the reaction was cooled, diluted with ice water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.250 g, 25%). MW=204.18. 1H NMR (DMSO-d6, 500 MHz) δ 8.26-8.18 (m, 2H), 8.05 (d, J=0.8 Hz, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.16 (s, 1H), 4.34 (s, 2H); APCI MS m/z 205 [M+H]+.

Workup

  1. temperatureAfter this time, the reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Sources & evidence

ORD record
ord-0cd4594167a24100aa1fe8653a3acc07
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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