Water → HCID 86604311, compound

HRID 1896049Notes

Reaction equation

HRID 1896049 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([S:32][CH3:33])=[N:25][C:26]([CH3:31])=[CH:27][C:28]=2[S:29][CH3:30])=[O:21])[CH2:15][CH2:14]1.[ClH:34].N1C=CC=CC=1.O>C(O)C>[OH2:21].[ClH:34].[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([S:32][CH3:33])=[N:25][C:26]([CH3:31])=[CH:27][C:28]=2[S:29][CH3:30])=[O:21])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 9892288K-604HCID 10176127Pyridinium chloride

Product 1

HCID 86604311HCID 86604311, compoundYield 176.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After heating and dissolving the free base (2.00 kg, 3.98 mol) of 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide and pyridine hydrochloride (0.92 kg, 7.96 mol) in ethanol (12 L) at reflux temperature, water (20 L) was added dropwise to the reaction mixture at 75 to 87° C. The reaction mixture was allowed to cool down to room temperature, and was stirred for 1 hour. Precipitated crystals were collected by filtration. The crystals were washed with water and dried at 80° C. under reduced pressure to obtain 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide monohydrochloride water adduct (1.96 kg, 89.0%; found to contain 2% of ethanol from 1H-NMR) as colorless needles.

Workup

  1. temperatureAfter heating
  2. additionwas added dropwise to the reaction mixture at 75 to 87° C
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washThe crystals were washed with water
  6. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-9307e189a6de4a7b92e29af9bffcf950
Source dataset
uspto-grants-2013_08
Patent number
US08518936B2

Reaction notes

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