Trimethyl phosphite → HCID 90383278, compound

HRID 874349Notes

Reaction equation

P(OC)(OC)OC.CN1CCCC1=O.F[C:16]([F:36])(F)/[C:17](=[N:24]\[C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][N:34]=1)[C:28]([O:30][CH3:31])=[O:29])/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[F:36][C:16]1[N:34]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]2=[N:24][C:17]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Trimethyl phosphite (1.9 ml) was added to an N-methylpyrrolidone (10 ml) solution of the (Z)-methyl 2-((2,2,2-trifluoro-1-phenylethylidene)amino)isonicotinate (2.5 g) obtained in (Example 2.19) <Step 1>, and the obtained mixture was then stirred in microwave at 150° C. for 60 minutes. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. Organic layers were gathered, and the gathered organic layer was then dried over sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=90:10-50:50), so as to obtain the title compound (1.9 g) in the form of a brown solid.

Workup

customobtained in (Example 2.19) <Step 1>
extractionthe mixed solution was then extracted with ethyl acetate
dry with materialthe gathered organic layer was then dried over sodium sulfate
distillationThe solvent was distilled away under reduced pressure
customthe obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=90:10-50:50)

Sources & evidence

ORD record: ord-1476b19fd7f643409b7bcd9ac1b2bda3
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980888B2

Reaction notes

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