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 1920127Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-0db4db9d85894a33a1931cd77632cdb9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168783B2

Reaction notes

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