Sodium Bicarbonate → HCID 11738567, compound

HRID 644520Notes

Reaction equation

HRID 644520 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=[N:16][C:12]=3[CH:11]=[C:10]([C:23](OCC)=[O:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+]>C(OCC)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=[N:16][C:12]=3[CH:11]=[C:10]([CH2:23][OH:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 11371743HCID 11371743, compound

Product 1

HCID 11738567HCID 11738567, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of lithium alumina hydride (0.24 g, 6.16 mmol) in anhydrous diethyl ether (20 ml) was added 7-(3-aminophenyl)-5-ethoxycarbonyl-1-phenylbenzimidazole (1.1 g, 3.08 mmol). Stirring was continued for 48 hours at ambient temperature in a nitrogen atmosphere. Aqueous sodium bicarbonate (2M) was added and the resultant mixture was extracted with ethyl acetate. This extract was dried over magnesium sulphate and concentrated under reduced pressure. The concentrate was eluted through silica gel with a mixture of ethyl acetate and methanol (9:1 v/v). Removal of solvent from the eluate left the title product as a yellow solid (0.38 g, 39%) m/z, 316.1 (M+H)+.

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. dry with materialThis extract was dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. washThe concentrate was eluted through silica gel with a mixture of ethyl acetate and methanol (9:1 v/v)
  5. customRemoval of solvent from the eluate
  6. waitleft the title product as a yellow solid (0.38 g, 39%) m/z, 316.1 (M+H)+

Sources & evidence

ORD record
ord-60772d5ef60f4db2a56580e1f93b6c82
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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