Hydrochloric Acid → HCID 49821381, compound

HRID 74165Notes

Reaction equation

HRID 74165 reaction equation
C([O:4][CH2:5][C:6]1[N:10]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:9]2[CH:17]=[CH:18][C:19]([C:21]3[S:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=3)=[CH:20][C:8]=2[N:7]=1)(=O)C.[OH-].[Li+].Cl>CO>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[C:19]1[CH:18]=[CH:17][C:9]2[N:10]([CH:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[C:6]([CH2:5][OH:4])=[N:7][C:8]=2[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 674980892-Acetoxymethyl-5-(benzothiazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

Product 1

HCID 49821381HCID 49821381, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A 4-neck flask (1 L) was charged with 2-acetoxymethyl-5-(benzothiazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 7-2) (5.00 g, 12.27 mmol), and methanol (253 mL), and an aqueous lithium hydroxide solution (1.0 M, 61 mL) was added at room temperature. After stirring under these conditions for 2 h, this was cooled in ice (0 to 10° C.) and dilute hydrochloric acid was added to the liquid to give an approximate pH of 5. The precipitated crystals were filtered off, washed with distilled water, and then dried under reduced pressure with heating to yield the title compound (4.28 g, 95.4% yield) as a greenish-white powder.

Workup

  1. customto give an approximate pH of 5
  2. filtrationThe precipitated crystals were filtered off
  3. washwashed with distilled water
  4. customdried under reduced pressure
  5. temperaturewith heating

Sources & evidence

ORD record
ord-79d857deb85c4129af6013c4a39f18ea
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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