Phosphorus oxide (P4O10) → HCID 178489867, compound

HRID 1760166Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[C:6]([NH:8][C:9]1[C:10]([CH3:20])=[N:11][NH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13]3[NH:12][N:11]=[C:10]([CH3:20])[C:9]=3[N:8]=2)[CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 160 °C

Procedure

128 mg of 3-methoxy-N-(3-methyl-5-phenyl-1H-pyrazol-4-yl)benzamide (4) were suspended in 5 ml of xylene and the suspension was boiled at 160° C.; 119 mg of phosphorus pentoxide were then added and the mixture was subsequently stirred at 160° C. for 15 min. 27 μl of phosphorus oxychloride were added dropwise to the suspension, which was then stirred at 160° C. for 12 h; a saturated solution of sodium hydrogen carbonate was then added and the whole was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, concentrated under reduced pressure and purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The following was obtained: 3. C18H15N3O (298.34); MS (ESI 290 (M+H)

Workup

stirringwas then stirred at 160° C. for 12 h
extractionthe whole was extracted with ethyl acetate
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
custompurified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)
customThe following was obtained

Sources & evidence

ORD record: ord-becbc504625148229d42f7e6b858e949
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841556B2

Reaction notes

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