Acetic Acid → HCID 86586554, compound

HRID 2119736Notes

Reaction equation

HRID 2119736 reaction equation
[CH3:1][C:2](N=N[C:8]([C:11]#N)([CH3:10])[CH3:9])([C:4]#[N:5])[CH3:3].[C:13](O)(=[O:15])C.[CH3:17][CH2:18][CH2:19]CCC.C1C[O:26]CC1>>[C:4]([C:2](=[CH2:3])[C:1]([O:15][CH3:13])=[O:26])#[N:5].[CH:8]12[CH2:9][CH:18]([CH2:19][CH2:10]1)[CH:17]=[CH:11]2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6547AzobisisobutyronitrileHCID 8028Tetrahydrofuran2×HCID 8058Hexane

Product 1

HCID 86586554HCID 86586554, compound

Procedure

To a 35 ml pressure tube equipped with a Teflon coated stir bar and a threaded Teflon cap with O-ring was added MCA (2.17 g, 19.5 mmol), NB (1.83 g, 19.5 mmol), THF (4 g), AIBN (120 mg) and acetic acid (200 mg). The reaction mixture was deaerated with nitrogen at a flow rate of 30 ml/min for 15 minutes. The reaction vessel was then immediately capped tight using the Teflon screw cap. The vessel was placed in an oil-bath, which was preheated to 72° C. The reaction was allowed to proceed for three hours. The viscous reaction mass was cooled to room temperature and diluted with 20.5 ml of THF. The solution was poured dropwise into 75 ml of hexane while stirring. The white polymer was filtered, washed with hexane and dried overnight in a vacuum oven at 55° C. The yield of the isolated polymer was 76.6%. The polymer was found to have a molecular weight of 11617 (Mw) with PD of 1.86.

Workup

  1. customTo a 35 ml pressure tube equipped with a Teflon coated stir bar
  2. customscrew cap
  3. customThe vessel was placed in an oil-bath
  4. customwas preheated to 72° C
  5. waitto proceed for three hours
  6. filtrationThe white polymer was filtered
  7. washwashed with hexane
  8. customdried overnight in a vacuum oven at 55° C

Sources & evidence

ORD record
ord-52ad9f69bde5496c8ea016d76318424b
Source dataset
uspto-grants-2004_02
Patent number
US06686429B2

Reaction notes

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