Acrylamide → HCID 6481627, compound

HRID 1072016Notes

Reaction equation

HRID 1072016 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1.[C:20]([NH2:24])(=[O:23])[CH:21]=[CH2:22]>N1C=CC=CC=1.CO.C(=O)(O)[O-].[Na+]>[N:11]1([CH2:10][C:2]2[N:1]([CH2:22][CH2:21][C:20]([NH2:24])=[O:23])[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1

Participants

6

Reactant 2

HCID 6579AcrylamideHCID 3822419HCID 3822419, compound

Product 1

HCID 6481627HCID 6481627, compoundYield 33.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-(1H-Benzimidazol-2-ylmethyl)-1H-benzotriazole (300 mg, 1.20 mmol) and acrylamide (86 mg, 1.20 mmol) were dissolved in pyridine (5 mL). Triton B (40% by weight in methanol, 0.010 mL, 0.024 mmol) was added at room temperature. The temperature was slowly raised to reflux. The reaction mixture was stirred at reflux overnight under nitrogen. The solvent was stripped under reduced pressure. The residue was taken up in aqueous saturated sodium bicarbonate solution and extracted with EtOAc (4×100 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography (EtOAc/MeOH 12:1 to 4:1) to give 128 mg (33%) of the title compound as a white solid.

Workup

  1. temperatureThe temperature was slowly raised
  2. temperatureto reflux
  3. temperatureat reflux overnight under nitrogen
  4. extractionextracted with EtOAc (4×100 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (EtOAc/MeOH 12:1 to 4:1)

Sources & evidence

ORD record
ord-a16addcbae434ab5ac6c24619b975e25
Source dataset
uspto-grants-2005_06
Patent number
US06908936B2

Reaction notes

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