Acetonitrile → HCID 67006090, compound

HRID 564343Notes

Reaction equation

HRID 564343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]2[CH2:23][CH2:24]I)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[C:27]#[N:28]>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]2[CH2:23][CH2:24][C:27]#[N:28])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 67006006HCID 67006006, compound

Product 1

HCID 67006090HCID 67006090, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-(4-chloro-benzenesulfonyl)-5,8-difluoro-3-(2-iodo-ethyl)-chroman (3.47 g, 6.94 mmol) in CH3CN (70 mL) was treated with n-Bu4NCN (2.2 g, 8.0 mmol). After 12 h, the reaction mixture was diluted with 1N HCl and extracted with Et2O (3×). The combined organic extracts were washed with 1N HCl (2×), saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo to afford the title compound (2.6 g, 94%): 1H NMR (CDCl3 400 MHz) δ 7.74 (dd, J=8.8, 2.2 Hz, 2H), 7.55 (dd, J=8.8, 2.2 Hz, 2H), 7.07 (m, 1H), 6.46 (m, 1H), 4.99 (dd, J=12.4, 2.9 Hz, 1H), 4.34 (dd, J=12.4, 2.2 Hz, 1H), 4.32 (s, 1H), 2.99 (t, J=6.6 Hz, 1H), 2.47 (t, J=7.3 Hz, 2H), 1.76 (m, 1H), 1.65 (m, 1H).

Workup

  1. extractionextracted with Et2O (3×)
  2. washThe combined organic extracts were washed with 1N HCl (2×), saturated aqueous NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cae3574358894f51ae710684584339c6
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

Loading…