Acrylamide → HCID 13797271, compound

HRID 1906070Notes

Reaction equation

HRID 1906070 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[K+].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>C1C=CC=CC=1.CN(C)C=O>[O:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6579AcrylamideHCID 7108PhenothiazineHCID 14797Potassium HydroxideHCID 12959377[(8-Bromooctyl)oxy]benzene

Product 1

HCID 13797271HCID 13797271, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Added to 20 ml of N,N-dimethylformamide were 0.62 g of acrylic amide and 2.0 g of (8-bromooctyloxy)benzene. With stirring, 0.49 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 amde. After they were reacted at 0°-5° C. for 6 hours, insoluble 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 1.53 g of N-(8-phenoxyoctyl)acrylic amide (yield: 79%). 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: 45°-47° C. Elementary analysis data: C, 74.21% (Calculated: 74.14%); H, 9.09% (9.15 %); N, 5.12% (5.09%).

Workup

  1. additionwas added
  2. customAfter they were reacted at 0°-5° C. for 6 hours
  3. custominsoluble 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-dd09fb38961c49f6ae1aededd412cdb2
Source dataset
uspto-grants-1987_03
Patent number
US04649219

Reaction notes

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