Tetrahydrofuran → HCID 66627756, compound

HRID 1471235Notes

Reaction equation

HRID 1471235 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][CH3:27].O1C[CH2:31][CH2:30][CH2:29]1>>[CH3:3][C:2]([C:4]1[N:5]([CH2:29][CH2:30][CH3:31])[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][CH3:27])[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)[CH3:1]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 66628016HCID 66628016, compound

Product 1

HCID 66627756HCID 66627756, compound

Procedure

To a flask were added 1.4 g 2,2′-propane-2,2-diylbis(1H-benzimidazole) and 30 ml tetrahydrofuran and the mixture was cooled to 10 C under nitrogen. 0.61 g Sodium hydride were added in portions and the reaction mixture was stirred for 20 minutes. 2.6 g 1-iodopropane were added and the mixture was stirred at 22 C for 3.5 hours. The mixture was quenched slowly with 30 ml water and stirred 16 hours. After cooling to 5 C, the solid was filtered and washed with water and purified by silica gel chromatography using 25% ethyl acetate in hexane to 50% ethyl acetate in hexane. 1.4 g of off-white solid was obtained.

Workup

  1. temperaturethe mixture was cooled to 10 C under nitrogen
  2. stirringthe mixture was stirred at 22 C for 3.5 hours
  3. customThe mixture was quenched slowly with 30 ml water
  4. stirringstirred 16 hours
  5. temperatureAfter cooling to 5 C
  6. filtrationthe solid was filtered
  7. washwashed with water
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-426993c630b647509a6c4cbad51464e9
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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