Acrylamide → N-t-Butylacrylamide Acrylamide

HRID 1018396

Reaction equation

HRID 1018396 reaction equation
[Cl-].C[N+](C)(C)CCOC(=O)C=C.[C:13]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])([CH3:16])([CH3:15])[CH3:14].[C:22]([NH2:26])(=[O:25])[CH:23]=[CH2:24]>C(O)(C)C>[C:13]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])([CH3:16])([CH3:15])[CH3:14].[C:22]([NH2:26])(=[O:25])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 7877tert-ButylacrylamideHCID 162071Ethanaminium, N,N,N-trimethyl-2-[(1-oxo-2-propen-1-yl)oxy]-, chloride (1:1)

Product 1

HCID 86584088N-t-Butylacrylamide Acrylamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

To a 500 mL round-bottom, three-neck flask fitted with a thermocouple, reflux condenser, and septum was added 150 mL of isopropanol followed by 16.13 g of a 50% aqueous solution of 2-trimethylammonioethylacrylate chloride, 8.06 g of N-t-butylacrylamide, and 8.06 g of acrylamide. The solution was purged with nitrogen for 1 hour and 0.5 g AIBN was added. The mixture was purged for ˜15 minutes until all of the AIBN dissolved. The solution was heated to 75° C. under nitrogen for 16 hours.

Workup

  1. customTo a 500 mL round-bottom, three-neck flask fitted with a thermocouple
  2. temperaturereflux condenser
  3. customThe solution was purged with nitrogen for 1 hour
  4. addition0.5 g AIBN was added
  5. customThe mixture was purged for ˜15 minutes until all of the AIBN
  6. dissolutiondissolved

Sources & evidence

ORD record
ord-531f7de438f842b5852c7c86a258570d
Source dataset
uspto-grants-2002_11
Patent number
US06482402B1

Linked notes

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