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 1897630Notes

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

Reaction notes

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