* 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.
15 mL (276 mmol, 6.6 eq) of concentrated sulfuric acid was slowly added dropwise to 8.40 g (41.8 mmol) of compound L5, Yellow bubbles, 10min after the drop is completed, At this time compound L5 is completely dissolved, The oil bath was heated at 80 ° C for 1 h and the reaction was stopped. Cold to room temperature, Add 150mL ice water, 4N NaOH aqueous solution adjusted to pH 7, At this time the original transparent solution in the precipitation of yellow solid, Filter, drying, Get 5.21g, The yield was 85.3percent. To give 1H-benzimidazole-2-formaldehyde,Compound code L6.
200 mesh hydroxyapatite powder, 0.008g as catalystUse 52 mL of hot water as solvent,The reaction was carried out with 0.1 mol o-phenylenediamine and 0.11 mol glyoxylic acid as raw materials. The reaction time was 6 hours and the reaction temperature was 52°C.After the reaction is over,Hot filter,Cool the filtrate to 2 °CWhite crystals precipitated,Filtered to obtain crystals,35 °C vacuum drying overnight,That is, benzimidazole-2-formaldehyde 11.9g, yield 81percent,Purity 99.6percent,
With [Ru(2,6-bis[1-(pyridin-2-yl)-1H-benzo[d]-imidazol-2-yl]pyridine)(pyridine-2,6-dicarboxylate)]; dihydrogen peroxide In water at 50℃; for 5.5 h;
The procedure for gram scale oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehydewas as follows: (1H-benzo[d]imidazol-2-yl)methanol (0.1 mol,14.8 g) and [Ru(bpbp)(pydic)] (0.001 mmol, 7.32 × 10−3 g) wereadded into a reactor. The reactor containing this mixture was heatedto 50 °C in an oil bath under vigorous stirring and then 30percent H2O2(30 mL, 0.3 mol) was slowly dropwise over a period of 30 min. The mixture was stirred for 5 h. After filtering, the solution wasevaporation under reduced pressure at 50 °C. Pure 1H-benzo[d]imidazole-2-carbaldehyde (0.07 mmol, 10.2 g) was obtained with ayield of 70percent after recrystallisation from 30percent H2SO4 solution. Theproduct, 1H-benzo[d]imidazole-2-carbaldehyde, was identified byits 1H NMR spectrum.
57%
at 50℃;
The method for synthesizing 2-aldehyde benzimidazole in this example is as follows2-Hydroxymethylbenzimidazole (0.1 mol, 14.8 g)The rhodium complex (10-4 mol, 0.0577 g) in Example 1 was added to the reaction vessel.Hydrogen peroxide (30percent, 0.3 mol, 9.1 ml) was slowly added to the reaction vessel with stirring.The reaction temperature was controlled at 50°C for several hours.The reaction solution was concentrated under reduced pressure,Obtain a solid product,The solid product was dissolved in dichloromethane and subjected to silica gel column chromatography.Get pure product2-aldehyde benzoimidazole 8.32 g,Yield 57percent.
51%
With manganese(IV) oxide In methanol; dichloromethane
General procedure: To a stirred solution of the (1H-benzo[d]imidazol-2-yl)methanol from above (2.6 mmol) in dryCH2Cl2/MeOH (6:1, 3.5 mL) was added activated manganese dioxide (85percent purity, <5 micron, 2.328 g, 22.8 mmol)and the suspension stirred overnight, at which point the black slurry was filtered through a cake of celite andwashed with MeOH (3x5 mL). The combined washings were concentrated to afford a dark brown solid.Purification of the crude product by column chromatography on silica gel (CH2Cl2:MeOH, 98:2 to 95:5) affordedthe title compound 1H-benzo[d]imidazole-2-carbaldehyde (2i) (0.245 g, 51percent).
Reference：
[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 12, p. 3128 - 3130
[2] Journal of Fluorescence, 2011, vol. 21, # 5, p. 2005 - 2013
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 12, p. 2871 - 2876
[4] Angewandte Chemie - International Edition, 1998, vol. 37, # 9, p. 1270 - 1273
[5] Journal of Chemical Research, 2017, vol. 41, # 2, p. 88 - 92
[6] Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 612 - 619
[7] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1765 - 1767
[8] Patent: CN107445998, 2017, A, . Location in patent: Paragraph 0028-0031
[9] Synthesis (Germany), 2015, vol. 47, # 13, p. 1913 - 1921
[10] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 577,594
[11] Molecules, 2016, vol. 21, # 11,
[12] Patent: CN107118249, 2017, A, . Location in patent: Paragraph 0120; 0121; 0122
[13] Patent: US5610299, 1997, A,
Reference：
[1] Journal of the Indian Chemical Society, 1982, vol. 59, # 3, p. 349 - 351
[2] Wiss. Z. Univ. Halle-Wittenberg, 1959, vol. 8, p. 1037
[3] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 577,594
With manganese(IV) oxide; In dichloromethane; at 40℃; for 2h;
To a solution of 1 (5.0 g, 34 mmol) in DCM was added MnO2(1.3 g, 6.8 mmol). The resulting solution was stirred at 40 C for 2 h and monitored by TLC. Aftercomplete conversion of starting material, reaction mixture was cooled to room temperature, filteredand concentrated in vacuo to obtain 2 as white solid in 85.0% yield. LC-MS m/z: 147.1 [M + H]+.
70%
With [Ru(2,6-bis[1-(pyridin-2-yl)-1H-benzo[d]-imidazol-2-yl]pyridine)(pyridine-2,6-dicarboxylate)]; dihydrogen peroxide; In water; at 50℃; for 5.5h;Catalytic behavior;
The procedure for gram scale oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehydewas as follows: (1H-benzo[d]imidazol-2-yl)methanol (0.1 mol,14.8 g) and [Ru(bpbp)(pydic)] (0.001 mmol, 7.32 × 10-3 g) wereadded into a reactor. The reactor containing this mixture was heatedto 50 C in an oil bath under vigorous stirring and then 30% H2O2(30 mL, 0.3 mol) was slowly dropwise over a period of 30 min. The mixture was stirred for 5 h. After filtering, the solution wasevaporation under reduced pressure at 50 C. Pure 1H-benzo[d]imidazole-2-carbaldehyde (0.07 mmol, 10.2 g) was obtained with ayield of 70% after recrystallisation from 30% H2SO4 solution. Theproduct, 1H-benzo[d]imidazole-2-carbaldehyde, was identified byits 1H NMR spectrum.
57%
With Ru(bpp)(pydic); dihydrogen peroxide; at 50℃;
The method for synthesizing 2-aldehyde benzimidazole in this example is as follows2-Hydroxymethylbenzimidazole (0.1 mol, 14.8 g)The rhodium complex (10-4 mol, 0.0577 g) in Example 1 was added to the reaction vessel.Hydrogen peroxide (30%, 0.3 mol, 9.1 ml) was slowly added to the reaction vessel with stirring.The reaction temperature was controlled at 50C for several hours.The reaction solution was concentrated under reduced pressure,Obtain a solid product,The solid product was dissolved in dichloromethane and subjected to silica gel column chromatography.Get pure product2-aldehyde benzoimidazole 8.32 g,Yield 57%.
51%
With manganese(IV) oxide; In methanol; dichloromethane;
General procedure: To a stirred solution of the (1H-benzo[d]imidazol-2-yl)methanol from above (2.6 mmol) in dryCH2Cl2/MeOH (6:1, 3.5 mL) was added activated manganese dioxide (85% purity, <5 micron, 2.328 g, 22.8 mmol)and the suspension stirred overnight, at which point the black slurry was filtered through a cake of celite andwashed with MeOH (3x5 mL). The combined washings were concentrated to afford a dark brown solid.Purification of the crude product by column chromatography on silica gel (CH2Cl2:MeOH, 98:2 to 95:5) affordedthe title compound 1H-benzo[d]imidazole-2-carbaldehyde (2i) (0.245 g, 51%).
With manganese(IV) oxide; In ethyl acetate; at 65℃; for 1h;
General procedure: A solution of 2a-2d (2 mmol), MnO2 (3.48 g, 40 mmol) was added to EtOAc (120 mL), then refluxedat 65 C for 1 h (monitored by TLC). Afterwards the solution was filtered, and concentrated in vacuoto give pure compounds 3a-3d (in 60%-76% yield) [17].
With manganese(IV) oxide; In dichloromethane; at 40℃; for 2h;
The resulting solid (1H-benzimidazol-2-yl) methanol (34 mmol) was dissolved in 250 mL of dichloromethane and stirredFollowed by addition of manganese dioxide (0.68 mmol). The temperature was raised to 40 C and stirring was continued for 2 hours to monitor the reaction. After the reaction is complete, the product is evaporated to drynessDichloromethane, 150 mL of tetrahydrofuran was added. Directly to the next step
With manganese dioxide; In N-methyl-acetamide; ethanol;
EXAMPLE I STR28 A mixture of 2-Hydroxymethyl-benzimidazole (11.9 g) and MnO2 (59.5 g) in ethanol (250 mL) was vigorously stirred for 2 days. The reaction was concentrated in vacuo, hot dimethylformamide was added and the mixture was filtered through celite. After removal of the solvent in vacuo the tan solid was triturated with ethanol to afford 2-Benzimidazolecarboxaldehyde as a tan powder.
15 mL (276 mmol, 6.6 eq) of concentrated sulfuric acid was slowly added dropwise to 8.40 g (41.8 mmol) of compound L5, Yellow bubbles, 10min after the drop is completed, At this time compound L5 is completely dissolved, The oil bath was heated at 80 ° C for 1 h and the reaction was stopped. Cold to room temperature, Add 150mL ice water, 4N NaOH aqueous solution adjusted to pH 7, At this time the original transparent solution in the precipitation of yellow solid, Filter, drying, Get 5.21g, The yield was 85.3percent. To give 1H-benzimidazole-2-formaldehyde,Compound code L6.
N-[(1E)-1H-benzimidazol-2-ylmethylene]-N-[2-(trifluoromethyl)benzyl]amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In methanol; acetic acid;
EXAMPLE 91 Preparation of N-[(1E)-1H-benzimidazol-2-ylmethylene]-N-[2-(trifluoromethyl)benzyl]amine (L-10) A mixture of 1.1 g (7.5 mmol) 1H-benzimidazole-2-carbaldehyde (Fluorochem), 1.3 g (7.5 mmol) 2-trifluoromethylbenzylamine and 1 drop glacial acetic acid in 10 ml methanol was stirred at room temperature for 72 hours. The resulted yellow solution was evaporated to c.a. 2-3 ml, cooled to -40° C. and the formed solid filtered. It was washed with methanol/water mixture (1/2) and dried under reduced pressure. Yield-1.96 g (86.4percent). 1H NMR (250 MHz, D2-DCM), delta: 5.03 (s, 2H), 7.28-7.69 (m, 8H), 8.46 (s, 1H).
EXAMPLE 19 Synthesis of 2-benzimidazolecarbaldehyde-(5-nitro-2-pyridyl)hydrazone (compound 19) A desired product was obtained in the same manner as in Example 1 by using 3.20 g (20.8 mmol) of 5-nitro-2-pyridylhydrazine and 2.90 g (19.8 mmol) of 2-benzimidazolecarbaldehyde. Yield: 4.80 g (17.0 mmol) [yield rate: 86percent] Melting point: 310° to 311° C.
3-(2-benzimidazolyl)-4-aminobutanoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In 2-(2-benzimidazolyl)-2-oxopyrrolidine;
EXAMPLE 30 3-(2-benzimidazolyl)-4-aminobutanoic acid By proceeding as in Example 1, but using 2-benzimidazolylcarbaldehyde in stage A of Example 1 instead of 2-(5-isopropyl)benzofurylcarbaldehyde, there are obtained: in STAGE C: 2-(2-benzimidazolyl)-2-oxopyrrolidine, and in STAGE D: the title compound.
Typical procedure for the preparation of Benzimidazolyl-benzimidazole; A solution of benzimidazole-2-aldehyde 1 (0.5 mmol) and diamine 2 (0.5 mmol) in dimethylacetamide (4mL) was stirred at 100 0C for 12h. Solvent was evaporated and residue was purified by preparative HPLC to give benzimidazole derivative 3. 1H NMR (300 <n="268"/>MHz, MeOH-doe : S 2.52 (s, 3H), 2.85 (brs, 4H)5 3.25 (brs, 4H)5 7.05-7.15 (m, 2 H), 7.25-7.35 (s overlapped with m, 2 H)5 7.60-7.75 (m, 4H); LCMS mlz 333 (M + H+), ELSD 99percent.
With triethylamine; In tetrahydrofuran; at 20℃; for 3.16667h;
2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)-1-(piperazin-1-yl)ethanone hydrochloride (Example 102) (150 mg, 0.315 mmol) was suspended in a mixture of tetrahydrofuran (3 ml) and triethylamine (0.052 ml, 0.378 mmol). 1H-benzo[d]-imidazole-2-carbaldehyde (55 mg, 0.378 mmol) was added at room temperature to the suspension, and the resulting mixture was stirred for 10 min. at room temperature. Sodium triacetoxyborohydride (267 mg, 1.26 mmol) was then added, and stirring was carried out for a further 3 d at room temperature. Saturated sodium hydrogen carbonate solution (5 ml) was added to the reaction mixture, and extraction with ethyl acetate (4.x.10 ml) was carried out. The organic phase was dried (MgSO4) and concentrated in vacuo, and the crude product was purified by column chromatography (silica gel) using ethyl acetate/methanol/ammonia solution (25percent aq.) (100:1:1). Yield: 60 mg (33percent), yellow solid; MS, m/z 570.3 (MH+)
With 4A molecular sieves; In ethanol; for 4h;Reflux;
59 B1 /-/-Benzimidazole-2-carboxaldehyde (781 mg, can be prepared according to Fegy, K. Angewandte Chemie Int Ed, 1998, vol. 37, 1270-1273), 4-amino-1 -methylpiperidine (781 mg) and 4A molecular sieves (15g) in ethanol (1 OOmL) are heated under reflux for 4h. The mixture is then filtered and the filtrate concentrated under reduced pressure to yield (1 - -benzimidazol-2-ylmethylene)(1 -methylpiperidin-4-yl)amine as a beige solid.
In ethanol; for 4h;Molecular sieve; Reflux;
1 H-Benzimidazole-2-carboxaldehyde (781 mg, can be prepared according to Fegy, K. Angewandte Chemie Int Ed, 1998, vol. 37, 1270-1273), 4-amino-1-methylpiperidine (781 mg) and 4A molecular sieves (15g) in ethanol (100mL) are heated under reflux for 4h. The mixture is then filtered and the filtrate concentrated under reduced pressure to yield (1H-benzimidazol-2-ylmethylene)(1-methylpiperidin-4-yl)amine as a beige solid.
With ammonium acetate; L-proline; In methanol; at 60℃; for 3h;
In a 50 mL round bottom flask 1,10-phenanthroline-5,6-dione (4.7 mmol), 1H-benzimidazole-2-carbaldehyde (5 mmol) and ammonium acetate (10 mmol) were taken in presence of 15 molpercent of L-proline in methanol (20 mL). Then the reaction mixture was stirred at 60 C for 3 h. After completion of the reaction, volume of the reaction mixture was reduced, diluted with water and extracted with ethyl acetate. Organic layer was dried over anhydrous MgSO4 and then solvent was removed under reduced pressure. Crude product was washed with n-hexane and recrystallized from ethanol to obtain the pure product. Anal. Calc. for C20H12N6: C, 71.42; H, 3.59; N, 24.99. Found: C,71.33; H, 3.62; N, 25.05percent;
General procedure: 2-(2-Aminomethyl)thiophene (5 mmol) dissolved in 5 mL of methanol was added dropwise to methanolic solution of 2-imidazole carbaldehyde (5 mmol). The mixture was allowed to stir at room temperature for 3 h, followed by dropwise addition of sodium borohydride (10 mmol) in 10 mL of sodium hydroxide solution. The resulting solution was stirred for 3 h and concentrated under reduced pressure; the residue was then extracted with three 10 mL portions of chloroform. The combined extract was dried over anhydrous MgSO4 and filtered, and the solvent was removed under reduced pressure to yield an oily product (L1). Yield: 0.466 g (62percent)
With hydrogenchloride; dihydrogen peroxide; 1,2-diamino-benzene; In water; acetonitrile; at 20℃; for 24h;
Bibenzimidazole (bbenzimH2) ligand was prepared by adopting the reported procedure [44]. Benzimidazolecarboxaldehyde (1 mmol, 146 mg) and ortho-phenylenediamine (1 mmol, 108 mg) were dissolved in acetonitrile. To this, 37 percent of HCl (3.5 mmol) was added, followed by the slow addition of aqueous solution of 30 percent hydrogen peroxide (700 mmol) to the mixture and then stirred for 24 h using magnetic stirrer under room temperature. Resulting solution was neutralized using ammonia solution to a pH 9. On standing, light brown yellow colored bbenzimH2 ligand was obtained which was then filtered and dried in vacuo. Yield: 79percent. Anal. Calc. for C14H10N4: C, 71.78; H, 4.30; N, 23.92. Found: C, 71.67; H, 4.40; N, 23.83percent. IR (KBr, mmax/cm-1): 3443vs (N?H). ESI-MS: m/z 235.27 ([L+H]+). Color: Pale yellow.
2,4-dimethylcarbonohydrazide bis-hydrochloride[ No CAS ]
[ 1611492-28-4 ]
Yield
Reaction Conditions
Operation in experiment
38%
In methanol; for 48h;Reflux;
A solution of 2-formylbenzimidazole (0.25 g, 1.71 mmol) inmethanol (5.5 mL) was added to a hot solution of 2,4-dimethylcarbonohydrazide bis-hydrochloride (0.20 g,1.71 mmol) in methanol (11 mL), and the mixture was heated atreflux for 48 h. At the end of 48 h, the reaction mixture was filteredand the solvent was evaporated under vacuum. The solid residuewas treated with ethyl acetate to give BIm2mVH3 as a yellow solid(0.16 g, 38percent, mp 205?207 C).
4-(5-fluoro-2-methoxyphenyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride[ No CAS ]
2-({4-[4-(5-fluoro-2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydropyridin-1(2H)-yl}methyl)-1H-benzimidazole trifluoroacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With ammonium acetate; acetic acid; In methanol; at 40℃;pH 4.0;
A 20 mL vial was charged with a 1.5 mL of ammonium acetate/acetic acid buffer solution (pH 4) in methanol. To this Example 87D (35.24 mg, 0.109 mmol) was added to form a suspension. lH-benzo[d]imidazole-2-carbaldehyde (23.89 mg, 1.5 eq, 0.164 mmol) and Si-BH3CN (from Silicycle, 0.88mmol/g loading, 371.49 mg) were then added. The vial was capped and placed to stir at 40°C overnight. Upon completion, the crude mixture was filtered, concentrated, and purified by HPLC (see Example 360 for protocols) to provide the title compound as a trifluoroacetic acid salt. lH NMR (400 MHz, pyridine-d5) delta ppm 2.57 (q, J = 4.1, 3.2 Hz, 2H), 2.83 (t, J = 5.7 Hz, 2H), 3.39 (q, J = 2.8 Hz, 2H), 3.71 (s, 3H), 4.17 (s, 2H), 6.61 (s, 1H), 6.64 - 6.67 (m, 1H), 7.09 (dd, J = 9.1, 4.5 Hz, 1H), 7.26 (ddd, J = 9.1, 7.9, 3.2 Hz, 1H), 7.32 (d, J = 4.9 Hz, 1H), 7.34 - 7.39 (m, 2H), 7.49 (dd, J = 8.9, 3.2 Hz, 1H), 7.89 (dd, J = 6.0, 3.2 Hz, 2H), 8.58 (d, J = 5.0 Hz, 1H). MS (ESI+) m/z 454.2 (M+H)+.
With potassium phosphate; In dimethyl sulfoxide; at 130℃; for 24h;Inert atmosphere;
General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.
With potassium phosphate; In dimethyl sulfoxide; at 130℃; for 24h;Inert atmosphere;
General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.
With potassium phosphate; In dimethyl sulfoxide; at 130℃; for 24h;Inert atmosphere;
General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.
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