Hydrochloric Acid → N-[3-(dimethylamino)propyl]acrylamide acrylamide N-dodecylacrylamide

HRID 379502

Reaction equation

HRID 379502 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:10])[CH:8]=[CH2:9].[C:12]([NH2:16])(=[O:15])[CH:13]=[CH2:14].[CH2:17]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl.Cl.N(C(C(=N)N)(C)C)=NC(C(=N)N)(C)C.Cl>O.C(O)C.C(O)(C)C>[CH3:11][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:10])[CH:8]=[CH2:9].[C:12]([NH2:16])(=[O:15])[CH:13]=[CH2:14].[CH2:17]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6579AcrylamideHCID 73929N-DodecylacrylamideHCID 763442,2'-Azobis(2-methylpropanimidamide) dihydrochlorideHCID 77452N,N-Dimethylaminopropyl acrylamide

Product 1

HCID 86757470N-[3-(dimethylamino)propyl]acrylamide acrylamide N-dodecylacrylamide

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of N-[3-(dimethylamino)propyl]acrylamide (22.5 g), acrylamide (2.7 g), and N-dodecylacrylamide (2.3 g) in deionized water (30 mL) and ethanol (30 mL) was heated to 60° C. under a nitrogen atmosphere. When the solution reached 60° C., 2,2′-azobis(2-amidinopropane)dihydrochloride (1.4 g of a 20 percent aqueous solution) was added. Heating was continued for 18 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction solution was dissolved in isopropanol (150 mL), and concentrated HCl (29.2 g) was added with stirring. The solution was decanted from the precipitated polymer. The polymer was suspended in isopropanol (500 mL), stirred for at least 15 minutes, and allowed to settle. After decanting, the polymer was similarly washed an additional 3 times with isopropanol. The washed polymer was dried in a forced-air oven at 70° C. to afford 34.7 g.

Workup

  1. customreached 60° C.
  2. temperatureHeating
  3. customThe solution was decanted from the precipitated polymer
  4. stirringstirred for at least 15 minutes
  5. customAfter decanting
  6. washthe polymer was similarly washed an additional 3 times with isopropanol
  7. customThe washed polymer was dried in a forced-air oven at 70° C.
  8. customto afford 34.7 g

Sources & evidence

ORD record
ord-2b62860f913e4f248f0e0a0dc4c5d1e1
Source dataset
uspto-grants-2001_10
Patent number
US06299868B1

Linked notes

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