Hydrochloric Acid → Methyl 4-(4,5-Dimethyl-3-oxido-1,3-oxazol-2-yl)benzoate

HRID 931410Notes

Reaction equation

HRID 931410 reaction equation
Cl.[CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3].[CH3:14][C:15](=[N:19][OH:20])[C:16](=O)[CH3:17]>CC(O)=O.CCOCC>[CH3:14][C:15]1[N+:19]([O-:20])=[C:2]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[O:3][C:16]=1[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15294Methyl 4-FormylbenzoateHCID 63989692-Oxime 2,3-butanedione

Product 1

HCID 68278194Methyl 4-(4,5-Dimethyl-3-oxido-1,3-oxazol-2-yl)benzoateYield 97.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

HCl gas was bubbled through a solution of methyl 4-formylbenzoate (8.20 g, 50.0 mmol) and 2,3-butanedione 2-oxime (5.05 g, 50 mmol) in HOAc (25 mL) at 0° C. and the mixture was stirred at 0° C. for 30 min. The mixture was diluted with Et2O (300 mL) and the resulting precipitate was filtered, washed with Et2O (50 mL) and dried in vacuo to give N-oxide 1 (12.05 g, 97%) as a white powder: mp (Et2O) 127-128° C.; 1H NMR (CDCl3) δ 8.44 (br d, J=8.8 Hz, 2H, H-2, H-6), 8.23 (br d, J=8.8 Hz, 2H, H-3, H-5), 3.98 (s, 3H, OCH3), 2.50 (s, 2H, CH3), 2.47 (s, 3H, CH3); MS m/z 248.6 (MH+, 100%).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with Et2O (50 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-2370b9df36e44d01951d8b83234c34f7
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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