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

HRID 713820Notes

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]

Participants

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

temperatureto be heated
temperatureAfter cooling
extractionextraction
dry with materialAfter being dried with anhydrous sodium sulfate
concentrationan organic phase is concentrated under reduced pressure
customto be separated
custompurified by liquid chromatography (SiO2, CHCl3:EtOAc=1:1)
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

Loading…