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2-Chloroethanol → 2-(1,1-Dicyanopropen-2-yl)-6-{[2-(2-hydroxy-ethoxy)-ethyl]methylamino}naphthalene

HRID 713820
Notes
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Reaction equation

HRID 713820 reaction equation
[C:1]([C:3]([C:21]#[N:22])=[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:16]([CH2:18][CH2:19][OH:20])[CH3:17])[CH:12]=2)[CH:7]=1)[CH3:5])#[N:2].Cl[CH2:24][CH2:25][OH:26]>C(#N)C>[C:1]([C:3]([C:21]#[N:22])=[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:16]([CH2:18][CH2:19][O:20][CH2:24][CH2:25][OH:26])[CH3:17])[CH:12]=2)[CH:7]=1)[CH3:5])#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 342-ChloroethanolHCID 18761122(1-(6-((2-Hydroxyethyl)(methyl)amino)-2-naphthyl)ethylidene)malononitrile

Product 1

HCID 1185093672-(1,1-Dicyanopropen-2-yl)-6-{[2-(2-hydroxy-ethoxy)-ethyl]methylamino}naphthaleneYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

0.40 g (1.4 mmol) of the fourth compound 4 is obtained to be dissolved in 8 mL of anhydrous acetonitrile. 0.35 g (4.3 mmol) of 2-chloro-ethanol is added to be heated with stirring at 80° C. for 17 hrs. After cooling, extraction is processed with dichloromethane. After being dried with anhydrous sodium sulfate, an organic phase is concentrated under reduced pressure to be separated and purified by liquid chromatography (SiO2, CHCl3:EtOAc=1:1). Thus, a product, 2-(1,1-dicyanopropen-2-yl)-6-{[2-(2-hydroxy-ethoxy)-ethyl]methylamino}naphthalene 5 (hereinafter referred to as fifth compound 5), is obtained, which has a weight of 0.29 g and a yield of 60.0%.

Workup

  1. temperatureto be heated
  2. temperatureAfter cooling
  3. extractionextraction
  4. dry with materialAfter being dried with anhydrous sodium sulfate
  5. concentrationan organic phase is concentrated under reduced pressure
  6. customto be separated
  7. custompurified by liquid chromatography (SiO2, CHCl3:EtOAc=1:1)
  8. customis obtained

Sources & evidence

ORD record
ord-5b82f0fe56ec4fe897ea5ebfaf8a2be3
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09186423B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes