1-Iodopropane → 6-[[1-(4-Methylphenyl)-2-propylmercapto-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

HRID 460515

Reaction equation

HRID 460515 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([SH:18])[N:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:14]=2[CH:26]=1.[CH2:28](I)[CH2:29][CH3:30].C(=O)([O-])O.[K+].C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3>CN(C)C=O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([S:18][CH2:28][CH2:29][CH3:30])[N:15]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)[C:14]=2[CH:26]=1

Participants

6

Reactant 4

HCID 336431-IodopropaneHCID 85955Dicyclohexano-18-crown-6HCID 516893Potassium BicarbonateHCID 178500330HCID 178500330, compound

Product 1

HCID 102960776-[[1-(4-Methylphenyl)-2-propylmercapto-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

1 g of 6-[[2-mercapto-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was dissolved in 15 ml of N,N-dimethylformamide, mixed with 0.3 ml of propyl iodide, 0.55 g of potassium hydrogen carbonate and 97 mg of dicyclohexano-18-crown-6, and the mixture was stirred for 48 hours at 20° C. It was filtered, and the filtrate was concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 1.06 g was obtained.

Workup

  1. filtrationIt was filtered
  2. concentrationthe filtrate was concentrated by evaporation in a vacuum
  3. customThe residue was purified by column chromatography on silica gel
  4. custom1.06 g was obtained

Sources & evidence

ORD record
ord-9ee6b961d3cb4359b6422ba934287ffa
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Linked notes

Loading…