Hydrochloric Acid → Benzimidazole

HRID 1404682Notes

Reaction equation

HRID 1404682 reaction equation
ClC1C=CC=CC=1CS([C:8]1[CH:29]=[CH:28][C:11]2[N:12](C(OC(C)(C)C)=O)[C:13](C3C=CC=CN=3)=[N:14][C:10]=2[CH:9]=1)(=O)=O.ClC1C=CC=CC=1CS(C1C=CC2N=C(C3C=CC=CN=3)N(C(OC(C)(C)C)=O)C=2C=1)(=O)=O.Cl.O1CCOCC1>CO.CCOCC>[NH:12]1[C:11]2[CH:28]=[CH:29][CH:8]=[CH:9][C:10]=2[N:14]=[CH:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68314965HCID 68314965, compoundHCID 68315153HCID 68315153, compound

Product 1

HCID 5798BenzimidazoleYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To stirred solution of tert-butyl 5-(2-chlorobenzylsulfonyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole-1-carboxylate (or the isomer, tert-butyl 6-(2-chlorobenzylsulfonyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole-1-carboxylate) (0.015 g, 0.031 mmol) in methanol (1 mL) was added 4N HCl in dioxane (0.155 μL, 0.62 mmol). The reaction mixture was stirred for 15 h at room temperature, diluted with Et2O (15 mL) and the white precipitate was filtered and dried under vacuum at 45° C. for 15 h to afford 8.4 mg of 5-(2-chlorobenzylsulfonyl)-2-pyridin-2-yl)-1H-benzo[d]imidazole (59%).

Workup

  1. filtrationthe white precipitate was filtered
  2. customdried under vacuum at 45° C. for 15 h

Sources & evidence

ORD record
ord-0163c5a20533453baf31c8f44f57ce21
Source dataset
uspto-grants-2014_12
Patent number
US08912336B2

Reaction notes

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