Methyl iodide → 2-(2-Methoxy-3-methyl-4-trifluoromethyl-phenyl)-3,4,4-trimethyl-4,5-dihydro-oxazol-3-ium iodide

HRID 659201Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1.[CH3:21][I:22]>[N+](C)([O-])=O.COC(C)(C)C>[I-:22].[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:6]=[CH:5][C:4]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N+:18]=1[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 447 mg (1.6 mmol) 2-(2-methoxy-3-methyl-4-trifluoromethyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole in 4 ml nitromethane was added 0.78 ml (12 mmol) methyl iodide and the mixture heated in a sealed tube to 60° C. for 18 h. The brown solution was diluted with tert-butyl methyl ether, the suspension filtered and the precipitate washed with tert-butyl methyl ether and dried. 2-(2-Methoxy-3-methyl-4-trifluoromethyl-phenyl)-3,4,4-trimethyl-4,5-dihydro-oxazol-3-ium iodide was obtained as off-white powder: MS (ISP): 302.1 (M+).

Workup

filtrationthe suspension filtered
washthe precipitate washed with tert-butyl methyl ether
customdried

Sources & evidence

ORD record: ord-299481cd53784d53acd9f93f376c7286
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080541B2

Reaction notes

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