1-Iodopentane → HCID 66626223, compound

HRID 1471266Notes

Reaction equation

HRID 1471266 reaction equation
[CH3:1][C:2]([C:13]1[NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]=1)([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1)[CH3:3].[H-].[Na+].I[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CN(C)C=O>[CH3:3][C:2]([C:4]1[N:5]([CH2:9][CH2:7][CH2:6][CH2:12][CH3:11])[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)([C:13]1[N:14]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)[CH3:1]

Participants

5

Reactant 3

HCID 123351-IodopentaneHCID 24758Sodium hydrideHCID 66628016HCID 66628016, compound

Product 1

HCID 66626223HCID 66626223, compoundYield 163.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.8 g 2,2′-Propane-2,2-diylbis(1H-benzimidazole) was added to 60 ml of N,N-dimethylformamide. 1.21 g Of a 60% sodium hydride dispersion in mineral oil was added in portions. 6.0 g Of 1-iodopentane was added and the mixture was stirred under nitrogen. After 4 hours, the reaction was quenched with 160 ml of water and then extracted with two 75 ml portions of ethyl acetate/methanol (˜99:1, v/v). The combined organic layers were washed twice with 75 ml of water. The cloudy organic layer was filtered. Following solvent removal to give a brown oil, the product was purified by silica gel chromatography increasing from 25% to 50% ethyl acetate in hexane by volume over the course of the elution. 3.46 g Of a yellow oil was obtained.

Workup

  1. customthe reaction was quenched with 160 ml of water
  2. extractionextracted with two 75 ml portions of ethyl acetate/methanol (˜99:1
  3. washThe combined organic layers were washed twice with 75 ml of water
  4. filtrationThe cloudy organic layer was filtered
  5. customFollowing solvent removal
  6. customto give a brown oil
  7. customthe product was purified by silica gel chromatography
  8. temperatureincreasing from 25% to 50% ethyl acetate in hexane by volume over the course of the elution

Sources & evidence

ORD record
ord-0788171c466149489ffeeaa9658d3436
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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