Aluminum(III) Chloride → HCID 58319011, compound

HRID 1750047Notes

Reaction equation

HRID 1750047 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1)=[C:2]=[S:3].[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[CH3:15][O:14][C:8]1[CH:7]=[C:6]2[C:11](=[C:10]([O:12][CH3:13])[CH:9]=1)[C:2](=[S:3])[NH:1][CH2:4][CH2:5]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 58319006HCID 58319006, compound

Product 1

HCID 58319011HCID 58319011, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 245 mg (1.10 mmol) of thioisocyanate 9 in 12 mL of methylene chloride was added 219 mg (1.65 mmol) of aluminum trichloride in one portion at 0° C. After stirring for 2.5 h at room temperature, the reaction mixture was quenched by dropwise addition of water. The layers were separated and the aqueous layer was extracted twice with 10-mL portions of methylene chloride. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed over silica gel (eluted with ethyl acetate) to afford 223 mg (91%) of 10 as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 6.44 (s, 1H), 6.30 (s, 1H), 3.92 (d, J=1.2 Hz, 3H), 3.85 (d, J=1.2 Hz, 3H), 3.40-3.32 (m, 2H), 2.93-2.83 (m, 2H).

Workup

  1. customthe reaction mixture was quenched by dropwise addition of water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with 10-mL portions of methylene chloride
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over silica gel (eluted with ethyl acetate)

Sources & evidence

ORD record
ord-1dc8d666d0be46bf8535a2c9c7cf18dc
Source dataset
uspto-grants-2015_10
Patent number
US09156836B2

Reaction notes

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