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2,2'-[(benzylimino)bis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide) → 2,2'-[iminobis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide)

HRID 1897630
Notes
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Reaction equation

HRID 1897630 reaction equation
C([N:8]([CH2:21][C:22]1[N:23]([S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH:24]=[CH:25][N:26]=1)[CH2:9][C:10]1[N:11]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH:12]=[CH:13][N:14]=1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].[C].C(O)C>[NH:8]([CH2:9][C:10]1[N:11]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:16])=[O:17])[CH:12]=[CH:13][N:14]=1)[CH2:21][C:22]1[N:23]([S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH:24]=[CH:25][N:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 675008132,2'-[(benzylimino)bis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide)

Product 1

HCID 672857942,2'-[iminobis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide)Yield 62.9%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To an ethanol (350 mL) solution of the compound (55.7 g) obtained in Example 2, 20% palladium hydroxide-carbon (13.6 g) was added under an argon atmosphere. The reaction mixture was stirred under a hydrogen atmosphere at 60° C. for 6 hours. The reaction mixture was cooled to room temperature and then filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→8:2) to obtain the title compound (28.5 g) having the following physical properties.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→8:2)

Sources & evidence

ORD record
ord-c71c9052d14e410981e6a72532e8672a
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08519124B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes