2-(3',4'-Diamino-biphenyl-2-sulfonyl)-ethanol → HCID 178504704, compound

HRID 1433228Notes

Reaction equation

HRID 1433228 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([S:15]([CH2:18]CO)(=[O:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].Cl.C(O[C:25](=N)[CH2:26][Br:27])C>C(O)C>[Br:27][CH2:26][C:25]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[S:15]([CH3:18])(=[O:16])=[O:17])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 579349382-(3',4'-Diamino-biphenyl-2-sulfonyl)-ethanolHCID 75357914Ethyl 2-bromoethanecarboximidate hydrochloride

Product 1

HCID 178504704HCID 178504704, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3′,4′-diamino-biphenyl-2-sulfonyl)-ethanol (0.140 g, 0.479 mmol) and 2-bromoacetimidic acid ethyl ester hydrochloride salt (0.116 g, 0.575 mmol) in anhydrous ethanol (100%, 6 mL) was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate and brine. The organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo to provide 2-bromomethyl-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole as yellow oil (0.178 g, 94%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1e8e12eb95b34590b901bf99812bdcc2
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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