[ CAS No. 33769-07-2 ] {[proInfo.proName]}

Name: 33769-07-2|(1-Trityl-1H-imidazol-4-yl)methanol|98%
Brand: Ambeed
SKU: A379401
Rating: 97 (26 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 33769-07-2 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 33769-07-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 33769-07-2 ]

SDS Specification

Alternatived Products of [ 33769-07-2 ]

Product Details of [ 33769-07-2 ]

CAS No. :	33769-07-2	MDL No. :	MFCD02179553
Formula :	C₂₃H₂₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DVQYFYUODSFBFS-UHFFFAOYSA-N
M.W :	340.42	Pubchem ID :	382182
Synonyms :

Safety of [ 33769-07-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 33769-07-2 ]

* 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.

Upstream synthesis route of [ 33769-07-2 ]
Downstream synthetic route of [ 33769-07-2 ]

[ 33769-07-2 ] Synthesis Path-Upstream 1~3

1
[ 28697-53-2 ]
[ 3473-63-0 ]
[ 76-83-5 ]
[ 15469-97-3 ]
[ 142822-28-4 ]
[ 33769-07-2 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 21, p. 4327 - 4346

2
[ 33769-07-2 ]
[ 33016-47-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sulfur trioxide pyridine complex; triethylamine In dimethyl sulfoxide at 20 - 110℃; for 1 h;	Step 8.b. 1-Triphenylmethyl-imidazole-4-carboxaldehyde The product from Step 8.a. (2.04 g, 6.00 mmol) was suspended in DMSO (10.0 ml) and Et3N (3.34 ml, 24.0 mmol) and SO3-pyridine complex (2.39 g, 15.0 mmol) were added at room temperature.. The mixture was warmed at about 110°C for about 1 hour and then allowed to cool.. The mixture was poured into 150 ml H2O and the product was filtered off.. The residue was treated with saturated NaHCO3 solution (50 ml) and extracted 2X 100 ml CH2Cl2.. The combined CH2Cl2 layers were washed with 5percent citric acid solution (100 ml), dried over Na2SO4, filtered and concentrated under reduced pressure.. The residue was crystallized from MeOH and H2O. Yield = 1.08g (53percent).
72.5%	With manganese dioxide In 1,4-dioxane	c (1-Triphenylmethyl-1H-imidazol-4-yl)carbaldehyde 68.1 g (0.2 mol) (1-triphenylmethyl-1H-imidazol-4-yl)-methanol and 177.9 g (2 mol) manganese dioxide are refluxed for 3 hours in 1.3 l dioxane. The hot suspension is filtered over 100 ml Celite in a Buchner funnel and washed with 0.5 l hot dioxane in three portions. The solution is evaporated in vacuo and the white solid residue dried in vacuo. Yield: 49.1 g (72.5percent), melting point: 188°-193° C.

Reference： [1] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 10, p. 1989 - 1998
[2] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 8, p. 1941 - 1944
[3] J. Med. Chem., 1996, vol. 39, # 2, p. 353 - 358
[4] Patent: EP1382607, 2004, A2, . Location in patent: Page 28
[5] Synthetic Communications, 1987, vol. 17, # 2, p. 223 - 228
[6] Tetrahedron, 2000, vol. 56, # 13, p. 1837 - 1850
[7] Collection of Czechoslovak Chemical Communications, 2002, vol. 67, # 9, p. 1335 - 1344
[8] Journal of Organic Chemistry, 2002, vol. 67, # 3, p. 620 - 624
[9] Patent: US2002/193596, 2002, A1,
[10] Patent: US5034539, 1991, A,

3
[ 33769-07-2 ]
[ 103057-10-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 20℃; Inert atmosphere	The product of the previous step 1-trityl-1H-imidazol-4-yl-methanol (2.3 g, 6.5 mmol)Add to pyridine(15 mL) to form a suspension,Thionyl chloride (2.0 mL, 20 mmol) was then added 5 times at room temperature for 30 min.Under nitrogen, the mixture was stirred overnight and the reaction solution became homogeneous, diluted with ethyl acetate (30 mL) and then dissolved with 5 wtpercent hydrochloric acidLiquid and saturated sodium carbonate solution. The organic phase was separated and anhydrous Na2SO4 was added to the organic phase. After filtration, the mixture was concentrated and evaporated.Solvent solvent1.8 g of white solid 4- (chloromethyl) -1-trityl-1H-imidazole in a yield of 93percent.

Reference： [1] Patent: CN106632268, 2017, A, . Location in patent: Paragraph 0033; 0034; 0036
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 2, p. 533 - 536
[3] Organic and Biomolecular Chemistry, 2006, vol. 4, # 9, p. 1768 - 1784
[4] Patent: US5965578, 1999, A,
[5] Patent: US4882343, 1989, A,
[6] Patent: US5891889, 1999, A,
[7] Patent: WO2018/191146, 2018, A1, . Location in patent: Paragraph 00402

[ 33769-07-2 ] Synthesis Path-Downstream 1~10

1
[ 822-55-9 ]
[ 76-83-5 ]
[ 33769-07-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;
93%	With triethylamine In N,N-dimethyl-formamide for 18h;
85%	Stage #1: (1H-imidazol-4-yl)methanol; trityl chloride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: With triethylamine In N,N-dimethyl-formamide for 16h; Inert atmosphere;	4-Hydroxymethyl-1-tritylimidazole (7) wasmade by two methods:(a) a modified, reported method was first used [9]. A hexanes solution(5.5 mL) of 1.0 M diisobutylaluminum hydride (Dibal-H) was addedto a THF solution (15 mL) of 6 (1.02 g, 2.72 mmol) under N2, and themixture was stirred for 1 h, and then cooled to 0 °C. The followingwere then slowly added in sequence: H2O (0.8 mL), 15% aq. NaOH(1.0 mL), and H2O (0.8 mL). Themixture was then filtered, and the precipitatewashed with THF (3 × 10 mL), the combined filtrate and washingsthen being evaporated in vacuo. The residue was dissolved inCH2Cl2 and the solution, after beingwashedwith H2O to remove any remaininginorganic salts,was evaporated in vacuo to give awhite productthatwas further dried for 24 h at r.t. in vacuo. Yield: 0.41 g (44%). (b) Toa stirred solution of 4-(hydroxymethyl)imidazole (0.52 g, 5.3 mmol) inDMF (10 mL) under N2 was added trityl chloride (1.48 g, 5.30 mmol),and after ~10 min NEt3 (0.90 mL, 6.4 mmol) was added. This mixturewas then stirred for 16 h, and poured onto ice; the resulting precipitatewas collected,washed withH2O(2×10mL), and dried in vacuo for 24 h.Yield: 1.53 g (85%). 1H NMR (CDCl3): δ 7.39 (s, 1H, H2-Im), 7.27-6.97(m, 15H, CPh3), 6.80 (s, 1H, H5-Im), 4.62 (s, 2H, CH2OH). ESI-MS: 341(M+), 243 (CPh3). Anal. Calcd. for C23H20N2O: C, 81.15; H, 5.92; N,8.23. Found: C, 81.2; H, 5.9; N, 7.9. The 1HNMR data agreewith reportedvalues [9].

83%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	Compound 5 To a stirred solution of 4(5)-(Hydroxymethyl)imidazole (1 g, 10.2 mmol) in anhydrous DMF (25mL), Et3N (2.13 mL) and trityl chloride (3.55 g, 12.7 mmol) were added and the mixture was stirred under argon atmosphere at room temperature for 12 h. The suspension was poured into of ice-cold water (80 mL) resulting in a formation of a white precipitate that was filtered, washed with cold Et2O and finally triturated with cold dioxane affording pure compound 5a (2.89 g, 83% yield). TLC RF = 0.19 (AcOEt). 1H NMR (400 MHz, DMSO-d6) δ 7.40 (q, J = 8.1, 7.2 Hz, 9H, Arom), 7.31 (s, 1H, H3), 7.09 (d, J = 7.4 Hz, 6H, Arom), 6.73 (s, 1H, H1), 4.89
76.8%	With triethylamine In dichloromethane at 50℃; for 4h;	2 (1-Trityl-1H-imidazol-4-yl)methanol (2) To a solution of (1H-imidazol-4-yl)methanol (0.5 g, 5.3 mmol) and Et3N (1.1 g, 10.2 mmol) in DCM (20 mL) was added TrCl (1.5 g, 5.3 mmol) and the mixture was stirred at 50° C. for 4 hours. TLC showed the reaction was completed. The reaction was cooled down, quenched with water (40 mL), extracted with DCM (5 mL×3). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography to give (1-trityl-1H-imidazol-4-yl)methanol (2) (1.0 g, yield: 76.8%) as colorless oil. 1H NMR (400 MHz, CHCl3-d) δ=7.37-7.44 (m, 9H), 7.29 (d, J=1.34 Hz, 2H), 7.10 (dd, J=8.01, 1.41 Hz, 6H), 4.87 (t, J=5.56 Hz, 1H), 4.33 (d, J=5.50 Hz, 2H)
69%	With pyridine at 50℃; for 24h;
59%	In dichloromethane at 20℃; for 18h;
56%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	10.1 Step 1: (1-trityl-1H-imidazol-4-yl)methanol To a solution of (1H-imidazol-4-yl)methanol (5.0 g, 51.0 mmol) and triethylamine (15.5 g, 152.9 mmol) in N,N-dimethylformamide (100 mL) was slowly added (chloromethanetriyl)tribenzene (15.6 g, 56.1 mmol). After addition, the reaction mixture was stirred at RT for 3 h and then poured into water (300 mL). The resulting solid was collected by filtration, washed with water (2 x 100 mL) and recrystallized with dioxane (300 mL) to afford (1-trityl-1H-imidazol-4-yl)methanol (9.8 g, 56% yield) as a white solid: 1H MR (400 MHz, DMSO-d6): δ 7.43 - 7.39 (m, 9H), 7.29 (s, 1H), 7.10 - 7.08 (m, 6H), 6.72 (s, 1H), 4.89 - 4.86 (m,- 4.32 (d, J= 5.6 Hz, 2H).
	With triethylamine In N,N-dimethyl-formamide
	With triethylamine In N,N-dimethyl-formamide
	With triethylamine In N,N-dimethyl-formamide
11.2 g (82%)	With N-ethyl-N,N-diisopropylamine In acetonitrile	6.C C. C. 1-(Triphenylmethyl)-1H-imidazole-4-methanol Diisopropylethylamine (14 mL, 80 mmol) was added dropwise to a suspension of 4-imidazole methanol (5.4 g, 40 mmol) in CH3 CN (15 mL) at 0° C. A homogeneous yellow solution was formed. To this solution was added triphenylmethyl chloride (11.2 g, 40 mmol). The reaction mixture was stirred at room temperature for 2 h. The resultant white precipitate was filtered and washed successively with saturated NaHCO3 aqueous solution (220 mL) and water (220 mL), then dried in a vacuum oven (45° C.) for 12 h to afford a white solid 11.2 g (82%) which was used in next step without further purification.
41 g (86%)	With triethylamine In 1,4-dioxane; <i>N</i>-methyl-acetamide	1.b b b (1-Triphenylmethyl-1H-imidazol-4-yl)methanol To a stirred solution of 18.8 g (140 mmol) (1H-imidazol-4-yl)methanol in 140 ml dimethylformamide and 50 ml triethylamine 40.5 g (145 mmol) triphenylmethylchloride in 300 ml dimethylformamide are dropped. After stirring for 2 hours at ambient temperature the reaction mixture is poured upon 2 kg of crushed ice. The precipitate is washed with water and impurities are removed by digestion with 400 ml warm dioxane. Collection, washing with diethyl ether and drying in vacuo yields 41 g (86%) of (1-Triphenylmethyl-1H-imidazol-4-yl)-methanol as a white powder, melting point: 224°-227° C.
	With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;	6.a Trityl chloride (45.57 g, 0.163 mol), (1 W-imidazol-4-yl)-methanol (20.00 g, 0.148 mol) and triethylamine (37.46 g, 0.370 mol) in DMF (150 ml_) are stirred at r.t. for 16 h, whereupon the mixture is poured into ice-cold water. The precipitate is filtered off and dried under high vacuum to give (1-trityl-1H-imidazol-4-yl)-methanol as a solid. Crude (1-trityl-1 W- imidazol-4-yl)-methanol (26.4 g, 0.077 mol), imidazole (15.88 g, 0.233 mol), DMAP (0.950 g, 7.7 mmol) and TBSCI (12.89 g, 0.085 mol) in DMF (0.1 L) are stirred at r.t. for 2 h, whereupon water is added. The mixture is extracted three times with dichloromethane. The organic layer is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel flash chromatography (elution with hexanes-ethyl acetate, 7:3) to yield 4-(tert-butyl- dimethyl-silanyloxymethyl)-1-trityl-1tf-imidazole as a white solid; MS (ESI) m/z 243, 455 (M+H).
	With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;	40.1 Step 1: (1-trityl-1H-imidazol-4-yl)methanol : [00401] To a solution of (1H-imidazol-4-yl)methanol (2.0 g, 20.39 mmol) in DMF( 30mL), was added and TrtCl(8.52g, 30.58 mmol) and TEA(4.13g, 40.77mmol), this mixture was stirred at rt for 18 h. The reaction solution was quenched with ice-water, filtered and triturated with PE to afford a white solid (5.5g, purity: 70%, yield:55.4%). ESI-MS (EI+, m/z): no MS was detected.

Reference： [1]Williams, Theresa M.; Bergman, Jeffrey M.; Brashear, Karen; Breslin, Michael J.; Dinsmore, Christopher J.; Hutchinson, John H.; MacTough, Suzanne C.; Stump, Craig A.; Wei, Donna D.; Zartman, C. Blair; Bogusky, Michael J.; Culberson, J. Christopher; Buser-Doepner, Carolyn; Davide, Joseph; Greenberg, Ian B.; Hamilton, Kelly A.; Koblan, Kenneth S.; Kohl, Nancy E.; Liu, Dongming; Lobell, Robert B.; Mosser, Scott D.; O'Neill, Timothy J.; Rands, Elaine; Schaber, Michael D.; Wilson, Francine; Senderak, Edith; Motzel, Sherri L.; Gibbs, Jackson B.; Graham, Samuel L.; Heimbrook, David C.; Hartman, George D.; Oliff, Allen I.; Huff, Joel R. [Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3779 - 3784]
[2]Hunt, John T.; Lee, Ving G.; Leftheris, Katerina; Seizinger, Bernd; Carboni, Joan; et al. [Journal of Medicinal Chemistry, 1996, vol. 39, # 2, p. 353 - 358]
[3]Kennedy, David C.; James, Brian R. [Inorganic Chemistry Communications, 2017, vol. 78, p. 32 - 36]
[4]Palmioli, Alessandro; Nicolini, Gabriella; Tripodi, Farida; Orsato, Alexandre; Ceresa, Cecilia; Donzelli, Elisabetta; Arici, Martina; Coccetti, Paola; Rocchetti, Marcella; La Ferla, Barbara; Airoldi, Cristina [Bioorganic Chemistry, 2021, vol. 109]
[5]Current Patent Assignee: PROVINCIAL HEALTH SERVICES AUTHORITY; UNIVERSITY OF BRITISH COLUMBIA; ESSA PHARMA INC - US2020/123117, 2020, A1 Location in patent: Paragraph 0968; 0969
[6]Bond, Roy F.; Bredenkamp, Martin W.; Holzapfel, Cedric W. [Synthetic Communications, 1989, vol. 19, # 13-14, p. 2551 - 2566]
[7]Houssin, Raymond; Pommery, Jean; Salaün, Marie-Catherine; Deweer, Sophie; Goossens, Jean-François; Chavatte, Philippe; Hénichart, Jean-Pierre [Journal of Medicinal Chemistry, 2002, vol. 45, # 2, p. 533 - 536]
[8]Current Patent Assignee: ROCHE HOLDING AG - WO2017/4500, 2017, A1 Location in patent: Page/Page column 132
[9]Adger, Brian M.; Surtees, John [Synthetic Communications, 1987, vol. 17, # 2, p. 223 - 228]
[10]Dinsmore, Christopher J.; Williams, Theresa M.; O'Neill, Timothy J.; Liu, Dongming; Rands, Elaine; Culberson, J. Christopher; Lobell, Robert B.; Koblan, Kenneth S.; Kohl, Nancy E.; Gibbs, Jackson B.; Oliff, Allen I.; Graham, Samuel L.; Hartman, George D. [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 23, p. 3301 - 3306]
[11]Peng, Hairuo; Carrico, Dora; Thai, Van; Blaskovich, Michelle; Bucher, Cynthia; Pusateri, Erin E.; Sebti, Said M.; Hamilton, Andrew D. [Organic and Biomolecular Chemistry, 2006, vol. 4, # 9, p. 1768 - 1784]
[12]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6156746, 2000, A
[13]Current Patent Assignee: BIOPROJECT; BIOPROJET; NATIONAL INSTITUTE OF HEALTH AND MEDICAL RESEARCH - US5034539, 1991, A
[14]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2007/117982, 2007, A2 Location in patent: Page/Page column 68-69
[15]Current Patent Assignee: NAVITOR PHARMACEUTICALS - WO2018/191146, 2018, A1 Location in patent: Paragraph 00401

2
[ 28697-53-2 ]
[ 3473-63-0 ]
[ 76-83-5 ]
[ 15469-97-3 ]
[ 142822-28-4 ]
[ 33769-07-2 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 4327 - 4346

3
[ 53525-60-3 ]
[ 33769-07-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 253 - 256

4
[ 61348-47-8 ]
[ 33769-07-2 ]
5-[2-(1-trityl-1H-imidazol-4-ylmethoxy)-phenyl]-isoxazole [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 3449 - 3452

5
[ 19311-91-2 ]
[ 33769-07-2 ]
N,N-diethyl-2-(1-trityl-1H-imidazol-4-ylmethoxy)-benzamide [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 3449 - 3452

6
[ 32673-41-9 ]
[ 76-83-5 ]
[ 33769-07-2 ]

Yield	Reaction Conditions	Operation in experiment
78%		Step 8.a. 4-Hydroxymethyl-1-triphenylmethyl-imidazole 4-Hydroxymethylimidazole hydrochloride (compound xiii where R2 is H) (2.50 g, 18.6 mmol) and Et3N (2.59 ml, 18.6 mmol) were combined in DMF (30 ml) and stirred at room temperature.. A solution of chlorotriphenylmethane (5.19 g, 18.6 mmol) in DMF (25 ml) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for about 23 hours and then poured into ice water (300 ml).. The product was filtered off, washed with cold water (75 ml) and triturated with p-dioxane (30 ml).. The product was filtered off and dried under reduced pressure to yield product (4.96 g, 78%). NMR (300MHZ, DMSO-d6, 30C) 7.3-7.5 (9H, m), 7.25-7.35 (1H, d), 7.0-7.2 (6H, m), 6.7-6.75 (1H, s), 4.15-4.2 (2H, m).
	With triethylamine; In N,N-dimethyl-formamide;	Step A 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.

	With triethylamine; In N,N-dimethyl-formamide;	Step A: Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.
	With triethylamine; In N,N-dimethyl-formamide;	Step J Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.
	With triethylamine; In N,N-dimethyl-formamide;	Step A: Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A 4-(Hydroxymethyl)-1-(triphenylmethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.
	With triethylamine; In N,N-dimethyl-formamide;	Step A 4-(Hydroxymethyl)-1-(triphenylmethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title product as a white.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vaculo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step B 1-Triphenylmethyl-4-(hydroxymethyl)imidazol To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl) imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 ml, of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step F 4-Hydroxymethyl-1-triphenylmethylimidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature is added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF is added dropwise. The reaction mixture is stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product is slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which is sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole (2) To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide 2 as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step E 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step J Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vccuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 ml) at room temperature was added triethylamine (90.6 ml, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 ml) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In dichloromethane;	(a) Triphenylmethyl chloride (2.78 g) was added to <strong>[32673-41-9]4-hydroxymethylimidazole hydrochloride</strong> (1.34 g) and triethylamine (2.8 ml) in dichloromethane (20 ml) stirred at 0 C. under an atmosphere of argon. The mixture was stirred for 18 hours and the insoluble solid was collected by filtration. The solid was washed well with water and dried under high vacuum to give 4-hydroxymethyl-1-triphenylmethyl-imidazole (B) as a white solid (2.4 g); NMR (90 MHz, d6 -DMSO): 4.3 (d, 2H), 4.8 (br t, 1H), 6.7 (S, 1H), 7.0-7.5 (complex m, 16H).
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In dichloromethane; at 20℃; for 18.0h;	(iii) (1-trityl-1H-imidazol-4-yl)methanol Trityl chloride (2.1 g) was added to a mixture of 4-hydroxymethyl imidazole hydrochloride (1.0 g) and triethylamine (3.1 ml) in DCM (25 ml) at RT. Further DCM (20 ml) was added and the mixture stirred for 18 h. The precipitate was filtered, washed with water and then ether to give the subtitle compound (2.0 g). 1H NMR DMSO-d6: delta 7.44-7.36 (9H, m), 7.29 (1H, s), 7.10-7.08 (6H, m), 6.72 (1H, s), 4.87 (1H, t), 4.33 (2H, d).
		Step A: 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step A: 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole. To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 ml) at room temperature was added triethylamine (90.6 ml, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 ml) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.
	With triethylamine; In N,N-dimethyl-formamide;	Step B 4-Hydroxymethyl-1-triphenylmethylimidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature is added triethylamine (90.6 mL, 650 mmol). A white solid precipitates from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF is added dropwise. The reaction mixture is stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product is slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product which is sufficiently pure for use in the next step.

Reference： [1]Patent: EP1382607,2004,A2 .Location in patent: Page 28
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 6812 - 6820
[3]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 1324 - 1326
[4]Patent: US2003/220241,2003,A1
[5]Patent: US2002/10184,2002,A1
[6]Patent: US2002/52363,2002,A1
[7]Patent: US2002/52380,2002,A1
[8]Patent: US2002/22633,2002,A1
[9]Patent: US6358985,2002,B1
[10]Patent: US6410534,2002,B1
[11]Patent: US6441017,2002,B1
[12]Patent: US6562823,2003,B1
[13]Patent: US6297239,2001,B1
[14]Patent: US5859012,1999,A
[15]Patent: US5859035,1999,A
[16]Patent: US5880140,1999,A
[17]Patent: US5856326,1999,A
[18]Patent: US5965578,1999,A
[19]Patent: US5977134,1999,A
[20]Patent: US6090948,2000,A
[21]Patent: US6015817,2000,A
[22]Patent: US6103723,2000,A
[23]Patent: US5972942,1999,A
[24]Patent: US6060038,2000,A
[25]Patent: US6015817,2000,A
[26]Patent: US6001835,1999,A
[27]Patent: US5710171,1998,A
[28]Patent: US5756528,1998,A
[29]Patent: US5780488,1998,A
[30]Patent: US5852010,1998,A
[31]Patent: US5756528,1998,A
[32]Patent: US5091425,1992,A
[33]Patent: US5780492,1998,A
[34]Patent: US6329376,2001,B1
[35]Patent: US2008/293775,2008,A1 .Location in patent: Page/Page column 21
[36]Patent: US2005/137207,2005,A1 .Location in patent: Page/Page column 93
[37]Patent: US5891889,1999,A
[38]Patent: US5891889,1999,A

7
[ 33769-07-2 ]
[ 103057-10-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine; thionyl chloride; at 20℃;Inert atmosphere;	The product of the previous step 1-trityl-1H-imidazol-4-yl-methanol (2.3 g, 6.5 mmol)Add to pyridine(15 mL) to form a suspension,Thionyl chloride (2.0 mL, 20 mmol) was then added 5 times at room temperature for 30 min.Under nitrogen, the mixture was stirred overnight and the reaction solution became homogeneous, diluted with ethyl acetate (30 mL) and then dissolved with 5 wt% hydrochloric acidLiquid and saturated sodium carbonate solution. The organic phase was separated and anhydrous Na2SO4 was added to the organic phase. After filtration, the mixture was concentrated and evaporated.Solvent solvent1.8 g of white solid 4- (chloromethyl) -1-trityl-1H-imidazole in a yield of 93%.
	With thionyl chloride; In chloroform;	Step G 4-Chloromethyl-1-triphenylmethylimidazole The product from Step F is dissolved in chloroform and cooled to 0 C. under nitrogen. Thionyl chloride (molar equivalent) is added slowly via syringe. The reaction is stirred for 30 min, and extracted with sodium bicarbonate solution. The organic phase is dried over magnesium sulfate, filtered and concentrated to provide the title compound.
	With thionyl chloride; triethylamine; In benzene;	(c) Synthesis of 1-trityl-4-chloromethyl-imidazole (3). To a solution of 2 g of 1-trityl-4-hydroxymethyl-imidazole (2) and 0.83 ml triethylamine in 25 ml anhydrous benzene these was dropwise added 0.41 ml of thionyl chloride. After 45 minutes of stirring at room temperature, the gas evolution has ceased. Then the precipitate was filtered and washed with benzene. The combined organic solutions were evaporated under reduced pressure. The residue was crystallized from dioxane yielding compound (3) used as such in the next stage.

	With thionyl chloride; In chloroform;	Step C 4-Chloromethyl-1-triphenylmethylimidazole The product from Step B is dissolved in chloroform and cooled to 0 C. under nitrogen. Thionyl chloride (molar equivalent) is added slowly via syringe. The reaction is stirred for 30 min, and extracted with sodium bicarbonate solution. The organic phase is dried over magnesium sulfate, filtered and concentrated to provide the title compound.
	With thionyl chloride; In dichloromethane; at 0 - 20℃; for 0.5h;	[00402] A solution of (1-trityl-1H-imidazol-4-yl)methanol (1.50g , 4.41mmol) in DCM (15 mL) was cooled to 0 C before adding SOCb (786.34 mg , 6.61mmol). DMF(483.12 mg, 6.61mmol) was added and the reaction mixture was stirred at rt for 30mins. The mixture was quenched with saturated NaHCCb solution, extracted with EtOAc, washed with brine, dried over sodium sulfate, and concentrated to afford the crude product as a yellow solid (1.5g) which was used directly in the next step. No MS was detected.

Reference： [1]Patent: CN106632268,2017,A .Location in patent: Paragraph 0033; 0034; 0036
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 533 - 536
[3]Organic and Biomolecular Chemistry,2006,vol. 4,p. 1768 - 1784
[4]Patent: US5965578,1999,A
[5]Patent: US4882343,1989,A
[6]Patent: US5891889,1999,A
[7]Patent: WO2018/191146,2018,A1 .Location in patent: Paragraph 00402

8
[ 33769-07-2 ]
[ 154312-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: MnO₂ / dioxane 2: 92 percent / NaNH₂ / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 20 h

Reference： [1]Adger, Brian M.; Surtees, John [Synthetic Communications, 1987, vol. 17, # 2, p. 223 - 228]

9
[ 822-55-9 ]
[ 76-83-5 ]
[ 822-55-9 ]
[ 33769-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 8h;	1.A Example 1; [4- (7-CYCLOPROPYLMETHYL-6-OXO-5,] 6,7, [8-TETRAHYDRO-IMIDAZO [1,] 5-a] [PYRAZIN-5-YL)-] benzonitrile; A. 1-Trityl-4-hydroxymethyl-1 H-imidazole To a stirred solution of 4 (5)-hydroxymethylimidazole (15.7 g, 117 [MMOL)] in DMF (200 mL) is added TEA (40.0 mL, 287 [MMOL)] followed by trityl chloride (34.3 g, 123 [MMOL).] The reaction mixture is stirred at RT for 8 h before it is poured into water. The collected solid is washed successively with water and diethyl ether and dried under reduced pressure. The solid is then re-crystallized from 1,4-dioxane to yield 1-trityl-4-hydroxymethyl-1 H-imidazole : m. p. [228-230°C] [; 1H-NMR (DMSO-D6) 6] 7.37 (9H, m), 7.35 (1 H, s), 7.09 (6H, m), 6.78 [(1 H, S),] 4.90 [(1H,] br s), 4.34 (2H, s); e/z (ES) 341 [(M+1,] 5%), 243 (100%).

Reference： [1]Current Patent Assignee: ELANCO ANIMAL HEALTH INC - WO2004/14914, 2004, A1 Location in patent: Page 32-33

10
[ 32673-41-9 ]
[ 76-83-5 ]
[ 121-44-8 ]
[ 33769-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	Step F Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 ml) at ambient temperature was added Et3 N (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step.

Reference： [1]Patent: US5817678,1998,A

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 33769-07-2 ]

Aryls

[ 106147-84-6 ]

(5-Methyl-1-trityl-1H-imidazol-4-yl)methanol

Similarity: 0.94

[ 1956369-41-7 ]

4-(Methoxymethyl)-1-trityl-1H-imidazole

Similarity: 0.94

[ 172498-89-4 ]

(1-Trityl-1H-imidazol-5-yl)methanol

Similarity: 0.94

[ 77134-74-8 ]

(1-Trityl-1H-imidazole-4,5-diyl)dimethanol

Similarity: 0.93

[ 62256-50-2 ]

1-(1-Trityl-1H-imidazol-4-yl)ethanol

Similarity: 0.92

Alcohols

[ 106147-84-6 ]

(5-Methyl-1-trityl-1H-imidazol-4-yl)methanol

Similarity: 0.94

[ 172498-89-4 ]

(1-Trityl-1H-imidazol-5-yl)methanol

Similarity: 0.94

[ 77134-74-8 ]

(1-Trityl-1H-imidazole-4,5-diyl)dimethanol

Similarity: 0.93

[ 62256-50-2 ]

1-(1-Trityl-1H-imidazol-4-yl)ethanol

Similarity: 0.92

Related Parent Nucleus of
[ 33769-07-2 ]

Imidazoles

[ 106147-84-6 ]

(5-Methyl-1-trityl-1H-imidazol-4-yl)methanol

Similarity: 0.94

[ 1956369-41-7 ]

4-(Methoxymethyl)-1-trityl-1H-imidazole

Similarity: 0.94

[ 172498-89-4 ]

(1-Trityl-1H-imidazol-5-yl)methanol

Similarity: 0.94

[ 77134-74-8 ]

(1-Trityl-1H-imidazole-4,5-diyl)dimethanol

Similarity: 0.93

[ 62256-50-2 ]

1-(1-Trityl-1H-imidazol-4-yl)ethanol

Similarity: 0.92

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 33769-07-2 ] {[proInfo.proName]}

Quality Control of [ 33769-07-2 ]

Related Doc. of [ 33769-07-2 ]

Product Details of [ 33769-07-2 ]

Safety of [ 33769-07-2 ]

Application In Synthesis of [ 33769-07-2 ]

[ 33769-07-2 ] Synthesis Path-Upstream 1~3

[ 33769-07-2 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 33769-07-2 ]

Aryls

Alcohols

Related Parent Nucleus of [ 33769-07-2 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 33769-07-2 ]

Related Parent Nucleus of
[ 33769-07-2 ]