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Chemical Structure| 19190-68-2 Chemical Structure| 19190-68-2

Structure of 19190-68-2

Chemical Structure| 19190-68-2

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Product Details of [ 19190-68-2 ]

CAS No. :19190-68-2
Formula : C8H8N2O
M.W : 148.16
SMILES Code : O=C1NC2=CC=CC(C)=C2N1
MDL No. :MFCD08274669
Boiling Point : No data available
InChI Key :HCHIWZADTVYYAR-UHFFFAOYSA-N
Pubchem ID :12501974

Safety of [ 19190-68-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 19190-68-2 ]

* 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.

  • Downstream synthetic route of [ 19190-68-2 ]

[ 19190-68-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 19190-68-2 ]
  • [ 15965-57-8 ]
YieldReaction ConditionsOperation in experiment
93% With trichlorophosphate; for 20h;Heating / reflux; 2-Hydroxy-4-methylbenzimidazole (5.92 g, 40 mmol) and 40 ml of phosphoryl chloride are introduced into a 250 ml two-necked flask under an argon atmosphere, equipped with a magnetic stirrer. The mixture is refluxed for 20 hours and the phosphoryl chloride is evaporated off under vacuum. The solid obtained is taken up in water (250 ml), the mixture is neutralized to pH=8 with 28% aqueous ammonia and the aqueous phase is extracted with ethyl acetate (3*250 ml). After the usual work-up, the 2-chloro-4-methylbenzimidazole is obtained in a yield of 93% (6.23 g). 1H NMR (300 MHz, delta ppm) DMSO-d6: 2.47 (s, 3H), 7.01 (d, 1H), 7.11 (t, 1H), 7.32 (d, 1H).
93% (6.23 g) With ammonium hydroxide; trichlorophosphate; In water; 1.4.2. 2-Chloro-4-methylbenzimidazole 2-Hydroxy-4-methylbenzimidazole (5.92 g, 40 mmol) and 40 mL of phosphoryl chloride are introduced into a 250 mL two-necked flask under an argon atmosphere, with magnetic stirring. The mixture is refluxed for 20 hours and the phosphoryl chloride is evaporated off under vacuum. The solid obtained is taken up in water (250 mL), neutralized to pH=8 with 28% aqueous ammonia and the aqueous phase is extracted with ethyl acetate (3*250 mL). After the usual work-up, the title product is obtained in a yield of 93% (6.23 g). 1H NMR (300 MHz, delta ppm) DMSO D6: 2.47 (s, 3H), 7.01 (d, 1H), 7.11 (t, 1H), 7.32 (d, 1H).
  • 2
  • [ 19190-68-2 ]
  • [ 15965-57-8 ]
YieldReaction ConditionsOperation in experiment
62% With trichlorophosphate; at 135℃; for 3h; Step A: 2-Chloro-4-methyl-l -benzo[d]imidazole To 4-methyl-lH-benzo[d]imidazol-2(3H)-one (1.5 g, 10 mmol) was added POCb (19 ml, 200 mmol) and the reaction mixture was heated to 135 C for 3 hours. The reaction was then cooled to room temperature and the excess POCb was removed in vacuo. The solid residue was diluted carefully with water and then slowly neutralized with saturated NaHCC until the pH was ~7-8. The mixture was extracted with ethyl acetate (2 x 150 mL) and the organics extracts were combined. The organics were dried with MgS04, filtered, and the solvent was removed to yield the crude residue. The crude material was purified by chromatography (Biotage) to yield 2-chloro-7-methyl-lH- benzo[d]imidazole (1.1 g, 6.3 mmol, 62 % yield) as a slightly yellow powder. MS (LC/MS) R.T. = 2.61 ; [M+]+ = 166.93
With hydrogenchloride; ammonium hydroxide; In chloroform; water; trichlorophosphate; Part B. 2-Chloro-4-methyl-1H-benzimidazole Hydrogen chloride gas was bubbled through a stirred mixture of 4-methyl-1H-benzimidazolidone (5 g, 0.034 mol) in phosphorus oxychloride (50 mL) for 1 hour at 120 C. The solvent was removed and the resulting solid was dissolved in water (50 mL). Ammonium hydroxide (20 mL) was carefully added until the mixture was basic. The aqueous phase was then extracted with chloroform, filtered through celite, and evaporated to give 5.2 g, of brown oil. The product was chromatographed on silica gel in chloroform, and was eluted with 1% methanol:chloroform to give 3.96 g of brown oil. Crystallization from ethyl acetate:hexane gave 2.72 g of brown crystals, mp 137.5-139.5 C.
With trichlorophosphate; at 95℃; for 1.5h; General procedure: A mixture of 5-methyl-1,3-dihydrobenzimidazol-2-one (1.00 g, 6.84 mmol) and phosphorous oxychloride (9.54 mL, 103 mmol) was stirred for 1.5 h at 95 C. After being cooled to ambient temperature, the reaction mixture was carefully added to a mixture of saturated NaHCO3 aq. (60 mL) and ethyl acetate (60 mL). The separated organic layer was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was evaporated in vacuo, The resulting precipitates were collected by filtration, and successfully washed with isopropyl ether to give 2-chloro-5-methyl-benzimidazole (1.74 g, 58.9 %).
 

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