Hydrochloric Acid → 5-(Benzothiazol-2-yl)-2-hydroxymethyl-1-phenylbenzimidazole

HRID 74156Notes

Reaction equation

HRID 74156 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:33]=[CH:32][C:13]2[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15]([CH2:17][O:18]CC3C=CC=CC=3)=[N:16][C:12]=2[CH:11]=1.Cl>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:33]=[CH:32][C:13]2[N:14]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:15]([CH2:17][OH:18])=[N:16][C:12]=2[CH:11]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 498212945-(Benzothiazol-2-yl)-1-phenyl-2-(phenylmethoxy)methylbenzimidazole

Product 1

HCID 498212955-(Benzothiazol-2-yl)-2-hydroxymethyl-1-phenylbenzimidazoleYield 94.3%

Procedure

An eggplant flask (50 mL) equipped with a reflux condenser was charged with 5-(benzothiazol-2-yl)-1-phenyl-2-(phenylmethoxy)methylbenzimidazole (see Working Example 1-2) (0.40 g, 0.89 mmol) and dilute hydrochloric acid (6 M, 5 mL), and this was refluxed for 2 hours. When the pale yellow clear solution obtained was cooled in ice, it became a milky white suspension. The precipitated crystals were filtered off, washed successively with distilled water, and then t-butyl methyl ether, and dried under reduced pressure to yield the title compound (0.30 g, 94% yield) as a white powder.

Workup

  1. customAn eggplant flask (50 mL) equipped with a reflux condenser
  2. temperaturethis was refluxed for 2 hours
  3. customWhen the pale yellow clear solution obtained
  4. temperaturewas cooled in ice
  5. filtrationThe precipitated crystals were filtered off
  6. washwashed successively with distilled water
  7. dry with materialt-butyl methyl ether, and dried under reduced pressure

Sources & evidence

ORD record
ord-16c4e80ba317466d8d2bca447a23c169
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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