(Diethylamino)sulfur trifluoride → 2-(1,1-Dicyanopropen-2-yl)-6-{[2-(2-fluoro-ethoxy)-ethyl]methylamino}naphthalene

HRID 713821Notes

Reaction equation

HRID 713821 reaction equation
[C:1]([C:3]([C:24]#[N:25])=[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][CH2:21][CH2:22]O)[CH3:17])[CH:12]=2)[CH:7]=1)[CH3:5])#[N:2].C(N(S(F)(F)[F:32])CC)C>C(Cl)Cl>[C:1]([C:3]([C:24]#[N:25])=[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][CH2:21][CH2:22][F:32])[CH3:17])[CH:12]=2)[CH:7]=1)[CH3:5])#[N:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 1185093672-(1,1-Dicyanopropen-2-yl)-6-{[2-(2-hydroxy-ethoxy)-ethyl]methylamino}naphthalene

Product 1

HCID 1185093702-(1,1-Dicyanopropen-2-yl)-6-{[2-(2-fluoro-ethoxy)-ethyl]methylamino}naphthaleneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.20 g (0.6 mmol) of the fifth compound 5 is obtained to be dissolved in 10 mL of anhydrous methylene chloride. 0.16 mL (1.2 mmol) of (diethylamino)sulfur trifluoride (DAST) is added at 0° C. for reaction at a room temperature for 16 hrs. After the reaction is completed, extraction is processed with water and dichloromethane. An organic phase is collected with water removed by sodium sulfate and is concentrated under reduced pressure to be separated and purified by liquid chromatography. Thus, the final product 6,2-(1,1-dicyanopropen-2-yl)-6-{[2-(2-fluoro-ethoxy)-ethyl]methylamino}naphthalene, is obtained, which has a weight of 0.12 g and a yield of 60.0%.

Workup

  1. extractionextraction
  2. customAn organic phase is collected with water
  3. customremoved by sodium sulfate
  4. concentrationis concentrated under reduced pressure
  5. customto be separated
  6. custompurified by liquid chromatography

Sources & evidence

ORD record
ord-9317fb5f11cb4175a22c83d7132a8e46
Source dataset
uspto-grants-2015_11
Patent number
US09186423B1

Reaction notes

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