HCID 19082053, compound → HCID 52951814, compound

HRID 2273637Notes

Reaction equation

HRID 2273637 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][N:3]=1.[CH3:12][S:13](OCCC1C=CN=C(F)C=1)(=[O:15])=[O:14]>>[CH3:12][S:13]([O:11][CH2:10][CH2:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1)(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 19082053HCID 19082053, compoundHCID 52951813HCID 52951813, compound

Product 1

HCID 52951814HCID 52951814, compoundYield 69%

Procedure

This compound was prepared, starting from compound 48 (5.00 g, 32.2 mmol), according to the procedure developed for compound 43. Reaction time at 0° C.: 30 min; the purification was performed using column chromatography (SiO2, AcOEt/pentane, 8/2, v/v) to give compound 49 (4.82 g, 20.7 mmol) as a yellow oil. Yield 69%; Rf (SiO2, AcOEt/pentane, 8/2, v/v) 0.58; IR (CCl4) ν 1179, 1351, 1371, 1413, 1613 cm−1; 1H NMR (200 MHz, CDCl3) δ 2.12 (m, 2H), 2.83 (t, 2H, J=7.3 Hz), 3.05 (s, 3H), 4.28 (t, 2H, J=6.1 Hz), 6.80 (s, 1H), 7.07 (m, 1H), 8.15 (d, 1H, J=5.1 Hz).

Workup

  1. customThis compound was prepared
  2. customReaction time at 0° C.
  3. custom30 min
  4. customthe purification

Sources & evidence

ORD record
ord-6cbee164c2904837973393b49d980772
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

Loading…