Structure of 671-01-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 671-01-2 |
| Formula : | C14H12FNO |
| M.W : | 229.25 |
| SMILES Code : | O=C(NCC1=CC=CC=C1)C2=CC=CC(F)=C2 |
| English Name : | N-Benzyl-3-fluorobenzamide |
| MDL No. : | MFCD00439111 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 73% | With dihydrolevoglucosenone; triethylamine at 0 - 20℃; for 1h; | |
| With N-ethyl-N,N-diisopropylamine In benzene at 20℃; for 0.166667h; Glovebox; Inert atmosphere; | ||
| 47 mg | With N-ethyl-N,N-diisopropylamine for 2h; Inert atmosphere; Glovebox; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 68% | With thionyl chloride for 2h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| kat. Zers. mit RhCl(P(C6H5)3)3 --> Nitrile + Alkohole; | ||
| Rk. mit RhCl(PPh3)3; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 68 percent / thionyl chloride / 2 h / Heating 2: 68 percent 3: 5 h / 160 °C | ||
| Multi-step reaction with 3 steps 1: 68 percent / thionyl chloride / 2 h / Heating 3: 5 h / 160 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 68 percent / thionyl chloride / 2 h / Heating 2: 68 percent | ||
| Multi-step reaction with 2 steps 1: 68 percent / thionyl chloride / 2 h / Heating |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 68 percent / thionyl chloride / 2 h / Heating |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: PCl5 |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 62% 2: 60% | With dichloro(benzene)ruthenium(II) dimer; N,N-diisopropylimidazolium bromide; sodium hydride In toluene; acetonitrile for 24h; Inert atmosphere; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With (1,2-dimethoxyethane)dichloronickel(II); phenylsilane In toluene at 115℃; for 24h; Inert atmosphere; Sealed tube; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | With C21H26N2O3Ru In toluene for 24h; Schlenk technique; Inert atmosphere; Glovebox; Reflux; | |
| 95% | With C20H26Cl2N2Ru; caesium carbonate In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux; Glovebox; | 2.2. General procedure for the NHC/Ru-catalyzed amide synthesisunder condition A General procedure: For the procedure applying a Ru loading of 1 mol%, an NHC-Rucomplex (one of [Ru-1]-[Ru-5], 0.005 mmol), Cs2CO3 (3.3 mg,0.01 mmol) and dry toluene (0.75 mL) were added to a 25 mL Schlenkflask inside an argon-filled glovebox. The Schlenk flask was equipped with a reflux condenser, which was sealed with a rubberseptum. The flask was taken out and subjected to three evacuatingrefilling(with argon) cycles in a Schlenk line before being heated toreflux under argon for 0.5 h to facilitate the formation of the correspondingNHC-Ru complex bearing a carbonate moiety [53]. Subsequently,alcohol 1 (0.50 mmol), amine 2 (0.55 mmol) wereadded into the flask, and the whole system was purged with Arfor 5 min. Finally, the flask was heated to reflux for another 24 h. |
| 81% | With [RhCl2(p-cymene)]2; 1-ethyl-3-methylbenzimidazolium iodide; sodium hydride In toluene; mineral oil for 36h; Schlenk technique; Inert atmosphere; Reflux; |
| 72% | With [Ru(p-cymene)Cl2]2; 1,3-dimethylbenzimidazolium Iodide; sodium hydride In toluene at 110℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; Reflux; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94% | With iron(II) chloride tetrahydrate In neat (no solvent) at 80℃; for 1.5h; | Typical experimental procedure for the reaction of nitriles and halohydrocarbons General procedure: A mixture of nitrile (10 mmol), halohydrocarbons (11 mmol) and FeCl2·4H2O (2 mol %) was placed in a round bottom flask. Then the reaction mixture was heated at 80 °C for the given time. After completion of the reaction monitored by thin layer chromatography (TLC), 5 ml water was added into reaction system and extracted with ethyl acetate (3 × 5 ml). The organic layers were collected, combined, washed with water (3 × 10 ml), dried over anhydrous Na2SO4, and concentrated under vacuum. The pure product was obtained by directly passing through a silica gel (200-300 mesh) column using petroleum ether/ethyl acetate and identified by 1HNMR and 13C NMR. |
| 92% | With zinc perchlorate In neat (no solvent) at 80℃; for 3h; | Reaction of nitriles and halohydrocarbons; typical procedure General procedure: CAUTION: Zn(ClO4)2.6H2O can cause skin and serious eye irritation and appropriate care should be taken in its use. In general, perchlorates are explosive compounds and appropriate caution should be taken including the avoidance of evaporation to dryness of perchlorate-containing residues. A mixture of the nitrile (1 mmol), halohydrocarbon (1.2 mmol) and Zn(ClO4)2·6H2O (5 mol%) was placed in a round-bottom flask. Then the reaction mixture was heated at 80 °C for the given time. After completion of the reaction (monitored by TLC), water (5mL) was added to the reaction mixture which was then extracted with ethyl acetate (3 × 5 mL). The organic layers were collected, combined, washed with water (3 × 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The pure product was obtained by passing the organic extract through a silica gel (200-300 mesh) column using petroleum ether (60-90 °C)/ethyl acetate (10:1-5:1) as eluent and identified by 1H NMR and 13C NMR. The 1H NMR and 13C NMR spectra of the products are shown in the Electronic Supplementary Information. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: (Xantphos)Pd(4-C6H4NO2)(I) / benzene / 20 h / 90 °C / Sealed tube; Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / benzene / 0.17 h / 20 °C / Glovebox; Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: (Xantphos)Pd(4-C6H4NO2)(I) / benzene / 20 h / 110 °C / Sealed tube; Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / benzene / 0.17 h / 20 °C / Glovebox; Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 89% | With iron (III) perchlorate monohydrate In neat (no solvent) at 80℃; for 5h; | Typical Experimental Procedure for the Reaction of VariousNitriles and Acetic Esters General procedure: A mixture of 3-methylbenzonitrile (5 mmol), benzyl acetate (6mmol), and Fe(ClO4)3·H2O (5 mol%) was placed in a round-bottomedflask. Then, the reaction mixture was heated at 80 °C for5 h. After completion of the reaction monitored by thin layerchromatography (TLC), water (10 mL) was added, and the reactionmixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were collected, combined, washed with water (3× 20 mL), dried with anhydrous Na2SO4, and concentrated undervacuum. The pure product was obtained by directly passingthrough a silica gel (200-300 mesh) column to give a whitepowder n (0.96 g, 86% yield). |