Hydrochloric Acid → HCID 67498488, compound

HRID 74167Notes

Reaction equation

HRID 74167 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:28]=[CH:27][C:13]2[N:14]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:15]([CH2:17][N:18]([CH3:20])[CH3:19])=[N:16][C:12]=2[CH:11]=1.O1CCOCC1.[ClH:35]>C(OCC)C>[ClH:35].[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:28]=[CH:27][C:13]2[N:14]([CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[C:15]([CH2:17][N:18]([CH3:20])[CH3:19])=[N:16][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67498000HCID 67498000, compound

Product 1

HCID 67498488HCID 67498488, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
2.5 °C

Procedure

An eggplant flask was charged with 5-(benzothiazol-2-yl)-2-(N,N-dimethylaminomethyl)-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 9) (0.176 g, 0.448 mmol), anhydrous diethyl ether (1 mL), and anhydrous 1,4-dioxane (7 mL), and this was stirred at 0 to 5° C. To this was added slowly a solution of hydrogen chloride in diethyl ether (2.0 M, 2 mL), after which this was stirred under these conditions for 30 minutes. The generated crystals were filtered off, these were then washed with diethyl ether (approx. 2 mL, 3 times) and dried under reduced pressure to yield the title compound (0.186 g, 96.9% yield) as a pale yellow powder.

Workup

  1. stirringafter which this was stirred under these conditions for 30 minutes
  2. filtrationThe generated crystals were filtered off
  3. washthese were then washed with diethyl ether (approx. 2 mL, 3 times)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-08c0235efdd740b281e5d5dbe4ce5c56
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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