Dimethylamine → N-((Dimethylamino)methyl)acrylamide

HRID 1577490Notes

Reaction equation

HRID 1577490 reaction equation
C=O.C(N)(=O)C=C.[OH-].[Na+].[CH2:10]([NH:12][C:13](=[O:16])[CH:14]=[CH2:15])O.[CH3:17][NH:18][CH3:19]>>[CH3:17][N:18]([CH2:10][NH:12][C:13](=[O:16])[CH:14]=[CH2:15])[CH3:19]

Participants

6

Reactant 5

HCID 674DimethylamineHCID 712FormaldehydeHCID 6579AcrylamideHCID 13543N-MethylolacrylamideHCID 14798Sodium Hydroxide

Product 1

HCID 75820N-((Dimethylamino)methyl)acrylamide

Conditions

Temperature
65 °C

Procedure

Into a reaction vessel as employed in Example 1 is added 13.3 parts of paraformaldehyde and 62.9 parts of a 48.1% aqueous solution of acrylamide. The pH is adjusted with aqueous NaOH to 11.5 and the homogeneous mixture allowed to stand 24 hours at room temperature. The product, >90 mole percent converted N-methylolacrylamide, is acidified to a pH of 2 and to it is added 57.5 parts of a 40% dimethylamine aqueous solution acidified to a pH of 2. The resulting solution is heated 3 hours at 65° C. and yields about 50 mole percent of N-(dimethylaminomethyl)acrylamide.

Workup

  1. customInto a reaction vessel as employed in Example 1

Sources & evidence

ORD record
ord-f0fb98faf5ae4834b5f43f85cb50ecc6
Source dataset
uspto-grants-1981_09
Patent number
US04288390

Reaction notes

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