Sodium Carbonate → HCID 178472061, compound

HRID 50301Notes

Reaction equation

HRID 50301 reaction equation
[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]([C:10]2[CH:29]=[CH:28][C:13]3[N:14]([CH3:27])[C:15]([CH2:17][NH:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:38][OH:39].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]([C:10]2[CH:29]=[CH:28][C:13]3[N:14]([CH3:27])[C:15]([CH2:17][NH:18][C:19]4[CH:24]=[CH:23][C:22]([C:25](=[NH:26])[NH:38][OH:39])=[CH:21][CH:20]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 443297Hydroxyamine hydrochloride2×HCID 184125221-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 178472061HCID 178472061, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.44 g (3.0 mmol) of 1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide, 0.625 g (9.0 mmol) of hydroxylamine hydrochloride and 0.425 g (4.0 mmol) of sodium carbonate were dissolved in 80 mL of ethanol and refluxed for 7 hours. Then a further 210 mg of hydroxylamine hydrochloride and 170 mg of sodium carbonate were added, the mixture was boiled for a further 5 hours and then evaporated down in vacuo. The residue was dissolved in about 30 mL of dichloromethane, the solution obtained was washed with 20 mL of water, the organic phase was dried and evaporated down. The crude product thus obtained was purified by column chromatography (200 g silica gel, dichloromethane +4% ethanol). Yield: 39% of theory, C28H30N6O4 (514.6); Rf value: 0.15 (silica gel; dichloromethane/ethanol=19:1); EKA mass spectrum: (M+H)+=515; (M+Na)+=537; (2M+H)+=1029; (2M+Na)+=1051.

Workup

  1. temperaturerefluxed for 7 hours
  2. customevaporated down in vacuo
  3. dissolutionThe residue was dissolved in about 30 mL of dichloromethane
  4. customthe solution obtained
  5. washwas washed with 20 mL of water
  6. customthe organic phase was dried
  7. customevaporated down

Sources & evidence

ORD record
ord-4377acc853b94304bb3b734114033101
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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