Acrylamide → N-(4-phenoxybutyl)acrylic amide

HRID 1906069Notes

Reaction equation

HRID 1906069 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].Br[CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>C1C=CC=CC=1.CN(C)C=O>[O:11]([CH2:10][CH2:9][CH2:8][CH2:7][NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6579Acrylamide2×HCID 7108PhenothiazineHCID 14797Potassium HydroxideHCID 70986(4-Bromobutoxy)benzene

Product 1

HCID 13650883N-(4-phenoxybutyl)acrylic amideYield 81.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Added to 20 ml of N,N-dimethylformamide were 1.34 g of acrylic amide and 3.4 g of (4-bromobutoxy)benzene. With stirring, 0.88 g of flaky potassium hydroxide which had been ground in a mortar was added. Phenothiazine was added in an amount of 0.5% based on the acrylic amide. After they were reacted at 0°-5° C. for 6 hours, insoluble matter was filtered off from the liquid reaction mixture. The solvent and unreacted raw materials were distilled off from the filtrate. The residue was extracted with benzene-water, thereby obtaining the intended product in the benzene layer. Benzene was then driven off from the benzene layer to obtain 2.66 g of N-(4-phenoxybutyl)acrylic amide (yield: 81%). It was purified further with column chromatography in which silica gel and benzene were used as an adsorbent and developer respectively. Its melting point was measured and its elementary analysis was also conducted. The following results were obtained. Melting point: 46°-47° C. Elementary analysis data: C, 71.29% (Calculated: 71.19%); H, 7.31% (7.82%); N, 6.15% (6.38%).

Workup

  1. additionwas added
  2. customAfter they were reacted at 0°-5° C. for 6 hours
  3. filtrationinsoluble matter was filtered off from the liquid reaction mixture
  4. distillationThe solvent and unreacted raw materials were distilled off from the filtrate
  5. extractionThe residue was extracted with benzene-water
  6. customobtaining the intended product in the benzene layer

Sources & evidence

ORD record
ord-71aba9a4503b4bf4900cc95103847716
Source dataset
uspto-grants-1987_03
Patent number
US04649219

Reaction notes

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