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Acrylamide → t-Butylacrylate Acrylamide

HRID 613196
Notes
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Reaction equation

HRID 613196 reaction equation
[Cl-].C[N+](C)(C)CCOC(=O)C=C.[C:13]([O: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]([O: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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 15458tert-Butyl acrylateHCID 162071Ethanaminium, N,N,N-trimethyl-2-[(1-oxo-2-propen-1-yl)oxy]-, chloride (1:1)

Product 1

HCID 86584091t-Butylacrylate 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 t-butylacrylate, 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-5a58c62c9040412d84b18bc447c2897b
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06007803

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes