Potassium Carbonate → Diacetone acrylamide oxime

HRID 1703051Notes

Reaction equation

HRID 1703051 reaction equation
[C:1]([NH2:5])(=O)[CH:2]=[CH2:3].[CH3:6][C:7]([CH3:9])=[O:8].[CH3:10][C:11]([CH3:13])=[O:12].Cl.[NH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>O>[C:1](=[N:15][OH:16])([NH2:5])[CH:2]=[CH2:3].[CH3:6][C:7]([CH3:9])=[O:8].[CH3:10][C:11]([CH3:13])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 215849214-Acrylamido-4-methyl-2-pentanone

Product 1

HCID 86738575Diacetone acrylamide oximeYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 408 g. (2.4 moles) of diacetone acrylamide ##STR12## and 200 g. (2.88 moles; 20% molar excess) of hydroxylamine hydrochloride in 1.5 l. of distilled water was added a solution of 200 g. (1.44 moles) of potassium carbonate in 250 ml. of water at room temperature of about 25° C. over a period of 15 min. A precipitate formed after about 15 minutes. Stirring was continued until a thick paste formed and the mixture was then allowed to stand for another hour. The solid product was isolated by filtration, washed with small portions of water (amounting to a total of 500 ml.) and dried at 40° C. in a vacuum oven. Yield of 365 g. of a white crystalline powder (82% yield), m.p. 103° C. The material was of sufficient purity to be directly employed in polymerization and was employed in the polymerization described in Example 2 hereinafter. If desired, further purification can be attained through recrystallization from benzene or toluene.

Workup

  1. customA precipitate formed after about 15 minutes
  2. customformed
  3. waitto stand for another hour
  4. customThe solid product was isolated by filtration
  5. washwashed with small portions of water (amounting to a total of 500 ml
  6. custom) and dried at 40° C. in a vacuum oven

Sources & evidence

ORD record
ord-648c20a8b2b74d7796dc575fd812d837
Source dataset
uspto-grants-1982_09
Patent number
US04350801

Reaction notes

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