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[ CAS No. 19190-68-2 ]

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Chemical Structure| 19190-68-2
Chemical Structure| 19190-68-2
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CAS No. :19190-68-2 MDL No. :MFCD08274669
Formula : C8H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :148.16 g/mol Pubchem ID :-
Synonyms :

Safety of [ 19190-68-2 ]

Signal Word:Warning Class:
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 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 19190-68-2 ]

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

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

  • 1
  • [ 19190-68-2 ]
  • [ 15965-57-8 ]
YieldReaction ConditionsOperation in experiment
62% at 135℃; for 3 h; 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 percent yield) as a slightly yellow powder. MS (LC/MS) R.T. = 2.61 ; [M+]+ = 166.93
Reference: [1] Patent: WO2016/73407, 2016, A1, . Location in patent: Page/Page column 56
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7188 - 7211
[3] Patent: US5273975, 1993, A,
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5010 - 5014
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1071 - 1074
  • 2
  • [ 19190-68-2 ]
  • [ 15965-57-8 ]
YieldReaction ConditionsOperation in experiment
93% for 20 h; 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 28percent 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 93percent (6.23 g).
1H NMR (300 MHz, δ 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 28percent 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 93percent (6.23 g).
1H NMR (300 MHz, δ ppm) DMSO D6: 2.47 (s, 3H), 7.01 (d, 1H), 7.11 (t, 1H), 7.32 (d, 1H).
Reference: [1] Patent: US2004/29866, 2004, A1, . Location in patent: Page/Page column 8
[2] Patent: US2003/203893, 2003, A1,
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