Phosphorus oxide (P4O10) → HCID 178489867, compound

HRID 719258Notes

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.

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-d8f26158fba4470582f238b8f32a9db0
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132428B2

Reaction notes

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