Hydrochloric Acid → HCID 118308834, compound

HRID 1481993Notes

Reaction equation

HRID 1481993 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13][CH:14]([N:17]=C(C1C=CC=CC=1)C1C=CC=CC=1)[C:15]#[N:16])[CH2:2][CH:3]=[CH2:4].Cl>C1COCC1.O>[NH2:17][CH:14]([CH2:13][C:7]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=1[O:5][CH2:1][CH2:2][CH:3]=[CH2:4])[C:15]#[N:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118308794HCID 118308794, compound

Product 1

HCID 118308834HCID 118308834, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-(but-3-en-1-yloxy)-5-fluorophenyl)-2-((diphenylmethylene)amino)propanenitrile (1.39 g, 3.49 mmol, 1 equiv) in THF (14 mL) was added 1 N HCl (3.84 mL, 3.84 mmol, 1.1 equiv). After 3 h, the reaction was diluted with water and washed with ether. The aqueous layer was then neutralized with 1 N NaOH and extracted with DCM (×3). The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo to provide the product (0.60 g, 73%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.00-6.92 (m, 2H), 6.85-6.77 (m, 1H), 5.90 (ddt, J=17.1, 10.2, 6.8 Hz, 1H), 5.20 (dd, J=17.1, 1.5 Hz, 1H), 5.15 (d, J=11.0 Hz, 1H), 4.12 (t, J=7.3 Hz, 1H), 4.03 (t, J=6.3 Hz, 2H), 3.05 (d, J=7.3 Hz, 2H), 2.57 (q, J=6.5 Hz, 2H), 2.19 (br. s., 2H).

Workup

  1. washwashed with ether
  2. extractionextracted with DCM (×3)
  3. dry with materialThe combined DCM extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6760c0819574969828a448002d7e664
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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