Sodium Carbonate → HCID 11441422, compound

HRID 277706Notes

Reaction equation

HRID 277706 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][NH:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15].C([O-])([O-])=O.[Na+].[Na+].[Cl:23][C:24]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C(OCC)(=O)C.CC(C)=O.O>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][N:11]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:26]([C:25]1[CH:29]=[CH:30][C:31]([O:35][CH3:36])=[C:32]([O:33][CH3:34])[C:24]=1[Cl:23])=[O:27]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 11481734HCID 11481734, compoundHCID 22625877HCID 22625877, compound

Product 1

HCID 11441422HCID 11441422, compoundYield 49.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 3.0 g (13.8 mmole) of (benzimidazol-2-ylmethyl) (3-methylbutyl)amine in 150 mL of 1:1:1 ethyl acetate, acetone, water is treated with 3.66 g (34.5 mmole) Na2CO3 and a solution of 3.22 g (13.7 mmole) of 2-chloro-3,4-dimethoxybenzoyl chloride in 50 mL of acetone at 0° C. The resulting mixture is allowed to warm to room temperature for 1 hour. The reaction solution is diluted with 300 mL of ethyl acetate and then washed with 2×60 mL water, 1×60 mL sat. NaHCO3, and 1×60 mL of brine. The resulting organic layer is dried over anhydrous Na2SO4 and the solvent removed in vacuo. The residue is treated with 150 mL of methanol and 1.1 g of NaOH at reflux for 2 hours and then allow to cool to room temperature for 2 hours. The resulting solution is evaporated under reduced pressure and partioned between ethyl acetate 200 mL and water 100 mL. The ethyl acetate extracts are dried over anhydrous Na2SO4 and the solvent removed in vacuo. The resulting residue is flash chromatographed (1:1 ethyl acetate/hexanes) to afford 2.82 g (49%) of N-(benzimidazol-2-ylmethyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide.

Workup

  1. customat 0° C
  2. washwashed with 2×60 mL water, 1×60 mL sat. NaHCO3, and 1×60 mL of brine
  3. dry with materialThe resulting organic layer is dried over anhydrous Na2SO4
  4. customthe solvent removed in vacuo
  5. additionThe residue is treated with 150 mL of methanol and 1.1 g of NaOH
  6. temperatureat reflux for 2 hours
  7. temperatureto cool to room temperature for 2 hours
  8. customThe resulting solution is evaporated under reduced pressure
  9. dry with materialThe ethyl acetate extracts are dried over anhydrous Na2SO4
  10. customthe solvent removed in vacuo
  11. customchromatographed (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1c101630bf214fa18c2b25526e438eb7
Source dataset
uspto-grants-2002_03
Patent number
US06358949B1

Reaction notes

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