Sodium Hydroxide → N,N-diethylglycine, [2[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]methyl ester

HRID 1493217Notes

Reaction equation

HRID 1493217 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][S:11]([C:13]2[N:17]([CH2:18][OH:19])[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[N:14]=2)=[O:12])[C:4]=1[CH3:24].Cl.[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][C:30](O)=[O:31])[CH3:27].[OH-].[Na+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.O>[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][C:30]([O:19][CH2:18][N:17]1[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[N:14]=[C:13]1[S:11]([CH2:10][C:5]1[C:4]([CH3:24])=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=1)=[O:12])=[O:31])[CH3:27]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 458470N,N-Diethylglycine hydrochlorideHCID 15282209HCID 15282209, compound

Product 1

HCID 57132605N,N-diethylglycine, [2[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]methyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A mixture of [2[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]methanol (3.5 g 0.010 mol), N,N-dicyclohexylcarbodiimide (2.1 g 0.010 mol), N,N-diethylglycine hydrochloride (1.7 g 0.010 mol) and 4-dimethylaminopyridine (1.3 g 0.011 mol) in pyridine (75 ml) was stirred at room temperature for 39 h. N,N-dicyclohexyl urea which had precipitated was removed by filtration. The filtrate was evaporated, the residue was dissolved in dichloromethane. The dichloromethanesolution was washed with NaOH 0.080 g (0.0020 mol), dissolved in water (25 ml) and then once with water (25 ml). The organic phase was dried (Na2SO4), filtered and the solvent was evaporated off, giving the desired product. The identity of the product was confirmed with NMR.

Workup

  1. customN,N-dicyclohexyl urea which had precipitated
  2. customwas removed by filtration
  3. customThe filtrate was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-f78da546feee4feda755d817dc5ff934
Source dataset
uspto-grants-1991_06
Patent number
US05021433

Reaction notes

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