1,2-Dichloroethane → HCID 68191111, compound

HRID 1615506Notes

Reaction equation

HRID 1615506 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[C:14]([C:16]2[S:17][C:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:19][CH:20]=2)=[O:15])\[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.ClCCCl.[Cl-].[Cl-].[Cl-].[Al+3]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C:20]3[CH:19]=[C:18]([C:21]4[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=4)[S:17][C:16]=3[C:14](=[O:15])[C@H:9]2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 6451240Aluminum(III) ChlorideHCID 68183184HCID 68183184, compound

Product 1

HCID 68191111HCID 68191111, compoundYield 44.8%

Conditions

Temperature
80 °C

Procedure

To a 20 mL vial was added a solution of methyl (2Z)-3-(4-chlorophenyl)-2-[(5-pyridin-4-yl-2-thienyl)carbonyl]acrylate (0.049 g, 0.128 mmol), in 1,2-dichloroethane (4.000 mL, 50.77 mmol). Aluminum trichloride (0.0340 g, 0.255 mmol) was added and the reaction mixture was heated to 80° C. and allowed to stir for 2 days. The reaction was cooled to ambient temperature and quenched by the addition of a saturated aqueous solution of sodium bicarbonate (5.00 mL) and extracted with EtOAc (10.00 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was dry loaded onto silica gel and then purified using ISCO (12 g cartridge, gradient hexanes to 100% EtOAc over 30 min) to afford the title compound (0.022 g, 43%) as a yellow oil. LC/MS (AA) ES+ 384, 386. 1H NMR (dmso-d6, 400 MHz): δ 8.66-8.65 (m, 2H), 7.81-7.78 (m, 3H), 7.45-7.34 (m, 4H), 4.96 (d, 1H), 4.13 (d, 1H), 3.72 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customquenched by the addition of a saturated aqueous solution of sodium bicarbonate (5.00 mL)
  3. extractionextracted with EtOAc (10.00 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dry with materialThe crude material was dry
  8. custompurified
  9. customISCO (12 g cartridge, gradient hexanes to 100% EtOAc over 30 min)

Sources & evidence

ORD record
ord-78d808f0a9b34c7c8397afab88bcfede
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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