Sulfuric Acid → DMAPMA t-Octyl Acrylamide

HRID 1451130Notes

Reaction equation

HRID 1451130 reaction equation
[CH:1]([N:3]1CCC[C:4]1=O)=C.[CH:9]([CH:11]1[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:12]1=[O:13])=C.CN(CCCC=C(C)C(N)=O)C.[C:31]([C:39](=[CH2:43])[C:40]([NH2:42])=[O:41])([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:32].OS(O)(=O)=O>C(O)C>[CH3:9][C:11]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:3]([CH3:4])[CH3:1])=[O:13])=[CH2:18].[C:31]([C:39](=[CH2:43])[C:40]([NH2:42])=[O:41])([CH2:34][C:35]([CH3:37])([CH3:38])[CH3:36])([CH3:32])[CH3:33]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6917N-vinyl-2-pyrrolidoneHCID 17881685Vinyl caprolactamHCID 190979953,3,5,5-Tetramethyl-2-methylidenehexanamideHCID 20976834Dimethylaminopropylmethacrylamide

Product 1

HCID 131719862DMAPMA t-Octyl Acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
68 °C

Procedure

Vinyl pyrrolidone (VP) (55.6 g), vinyl caprolactam (VCL) (577.5 g), dimethylaminopropyl methacrylamide (DMAPMA) (42.6 g), tert-octyl acrylamide (18.3 g) and ethanol (848.2 g) were charged into a 2-liter water-jacketed resin flask. The reaction flask was equipped with a condenser, a thermometer, a septum (for catalyst addition), an anchor-type metal stirrer, and a nitrogen sparge tube. Nitrogen was bubbled the solution while the resin flask was heated to 68° C. using hot water circulating through the jacketed flask. After an additional half-hour of degassing at reflex, a first shot of Lupersol 11 (0.25 ml) was injected into the flask. Subsequently, Lupersol 11 additions were made at 10, 40, 70, 100 minutes after the first addition. The reaction temperature was increased to 74° C. and 2 shots of Lupersol 554 M75 (0.12 ml) was then added at 240 and 330 minutes. The contents were allowed to react for an additional 5 hours and cooled to 35°-40° C. After neutralization with 12.5 g of H2SO4 (conc) the product was discharged as a 45% solution in ethanol.

Workup

  1. customThe reaction flask was equipped with a condenser
  2. additiona thermometer, a septum (for catalyst addition)
  3. customan anchor-type metal stirrer, and a nitrogen sparge tube
  4. customNitrogen was bubbled the solution while the resin flask
  5. customAfter an additional half-hour of degassing at reflex
  6. customwere made at 10, 40, 70, 100 minutes
  7. additionafter the first addition
  8. temperatureThe reaction temperature was increased to 74° C.
  9. addition2 shots of Lupersol 554 M75 (0.12 ml) was then added at 240 and 330 minutes
  10. customto react for an additional 5 hours
  11. temperaturecooled to 35°-40° C

Sources & evidence

ORD record
ord-aada65a6c6c14473874b325d5557bf70
Source dataset
uspto-grants-1997_02
Patent number
US05603919

Reaction notes

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