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3-Ethoxy-2-propenoyl chloride → 3-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamide

HRID 472158
Notes
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Reaction equation

HRID 472158 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[CH2:14]([O:16][CH:17]=[CH:18][C:19](Cl)=[O:20])[CH3:15]>N1C=CC=CC=1>[CH2:14]([O:16][CH:17]=[CH:18][C:19]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[CH:8][CH:9]=1)=[O:20])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 30144293-Ethoxy-2-propenoyl chlorideHCID 31574784-(2-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 672049713-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamideYield 92.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-methyl-1H-imidazol-1-yl)aniline (40.7 g, 232 mmol; RN: 74852-81-6, Maybridge, J. Med. Chem., 48(6), 1729-1744; 2005) was dissolved in dry pyridine (290 mL), 3-ethoxyacryloyl chloride (36.1 g, 268 mmol) was then added dropwise at 0°/−10° C. The resulting mixture was stirred at 0° C. for 2 hours and at r.t. overnight. The reaction mixture was quenched with 100 mL of water, and pyridine was distilled i.v., the residue was taken up with water and the pH was adjusted to pH=10, by adding K2CO3, the resulting suspension was extracted with AcOEt and concentrated. The resulting solid was stirred with hexane and filtered to afford the title product (58 g; 92%). C15H17N3O2, MW: 271.32.

Workup

  1. customThe reaction mixture was quenched with 100 mL of water, and pyridine
  2. distillationwas distilled i.v
  3. additionby adding K2CO3
  4. extractionthe resulting suspension was extracted with AcOEt
  5. concentrationconcentrated
  6. stirringThe resulting solid was stirred with hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-32752ba40a4a416784d226bcd7e05e8b
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633208B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes