N-methyl-2-pyrrolidone → Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

HRID 2084623Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5](Br)=[CH:6][CH:7]=1.CN1C(=O)CCC1.[CH3:22][S-:23].[Na+]>O>[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5]([S:23][CH3:22])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

25 g (0.075 mol) of 3-(3,6-dibromo-2-methylphenyl)-4,5-dihydroisoxazole are initially charged in 12 mol of NMP. At a temperature of 100° C. and at a reduced pressure of 100 mbar, 29.3 g (0.09 mol) of a 21.5% strength methanolic solution of sodium thiomethoxide are added dropwise over a period of 40 min. The reaction mixture is stirred at 100° C. for 3 h and then stirred into 250 ml of water and extracted three times with 100 ml of toluene. The combined organic phases are washed once with 100 ml of water and then concentrated under reduced pressure. This gives 17.5 g of a dark oil. GC/MS shows, in addition to other isomers, 52.3% of the desired product. MSm/z: 287.

Workup

extractionextracted three times with 100 ml of toluene
washThe combined organic phases are washed once with 100 ml of water
concentrationconcentrated under reduced pressure
additionGC/MS shows, in addition to other isomers, 52.3% of the desired product

Sources & evidence

ORD record: ord-78e7671ab2d74c91a1ebf11a8c968798
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716989B2

Reaction notes

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