Hydrochloric Acid → 2,2'-[[(4-formylbenzyl)imino]bis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide)

HRID 445234Notes

Reaction equation

HRID 445234 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:36]=[CH:35][C:8]([CH2:9][N:10]([CH2:23][C:24]2[N:25]([S:29]([N:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[CH:26]=[CH:27][N:28]=2)[CH2:11][C:12]2[N:13]([S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH:14]=[CH:15][N:16]=2)=[CH:7][CH:6]=1)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:23][C:24]2[N:25]([S:29]([N:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[CH:26]=[CH:27][N:28]=2)[CH2:11][C:12]2[N:13]([S:17]([N:20]([CH3:22])[CH3:21])(=[O:18])=[O:19])[CH:14]=[CH:15][N:16]=2)=[CH:35][CH:36]=1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 672847312,2'-[{[4-(diethoxymethyl)benzyl]imino}bis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide)

Product 1

HCID 866644642,2'-[[(4-formylbenzyl)imino]bis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide)Yield 85.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,2′-[{[4-(diethoxymethyl)benzyl]imino}bis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide) (International Publication WO 2007/058322 pamphlet, Example 27; 10.0 g), ethyl acetate (100 mL) and 2N hydrochloric acid (100 mL) were added, followed by stirring at room temperature for 3 minutes. The aqueous layer was neutralized with an aqueous saturated sodium carbonate solution, extracted with ethyl acetate and then washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound (7.46 g) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0f0ba4e27d44f08a1c62eb52b8461e3
Source dataset
uspto-grants-2013_07
Patent number
US08476290B2

Reaction notes

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