HCID 25151979, compound → HCID 25151977, compound

HRID 1968680Notes

Reaction equation

HRID 1968680 reaction equation
[Cl-:1].[NH2:2][C:3]1[CH:8]=[CH:7][N+:6]([CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([S:20](=[O:30])(=[O:29])[N:21]([CH3:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]=[CH:16][C:15]=2[NH:31][CH3:32])=O)=[CH:5][CH:4]=1>C(#N)C.S(Cl)(Cl)=O.C(OCC)C>[Cl-:1].[NH2:2][C:3]1[CH:8]=[CH:7][N+:6]([CH2:9][CH2:10][C:11]2[N:31]([CH3:32])[C:15]3[CH:16]=[CH:17][C:18]([S:20](=[O:30])(=[O:29])[N:21]([CH3:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:19][C:14]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 25151979HCID 25151979, compound

Product 1

HCID 25151977HCID 25151977, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a suspension of 4-amino-1-(3-(5-(N-methyl-N-phenylsulfamoyl)-2-(methylamino)phenylamino)-3-oxopropyl)pyridinium chloride (0.2 g, 0.00042 mol) in acetonitrile (8 ml), thionyl chloride (0.2 ml) was added. After boiling the reaction mixture for 10 min, it was left to stand at room temperature for 24 h and then diluted with diethyl ether (8 ml). The precipitate formed was collected by filtration and crystallized from a 10:1 mixture of acetonitrile with dehydrated ethanol. The yield of 4-amino-1-(2-(1-methyl-5-(N-methyl-N-phenylsulfamoyl)-1H-benzo[d]imidazol-2-yl)ethyl)pyridinium chloride was 0.055 g (26%).

Workup

  1. additionwas added
  2. customfor 10 min
  3. waitit was left
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. customcrystallized from a 10:1 mixture of acetonitrile with dehydrated ethanol

Sources & evidence

ORD record
ord-b30b07bedaab4a179ec980409e9cb4a7
Source dataset
uspto-grants-2013_04
Patent number
US08426433B2

Reaction notes

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