Benzoyl chloride → HCID 22225917, compound

HRID 1744900Notes

Reaction equation

HRID 1744900 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[S:10][C:11]=1[CH3:12].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCCl>[C:17]([C:8]1[C:7]([CH3:6])=[C:11]([CH3:12])[S:10][C:9]=1[NH:13][C:14](=[O:16])[CH3:15])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24287Tin tetrachlorideHCID 2408995HCID 2408995, compound

Product 1

HCID 22225917HCID 22225917, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

General Method A. A solution of 1.71 M tin (IV) chloride (3.1 mL, 5.3 mmole) in 1,2-dichloroethane was added dropwise to a suspension of 9 (0.241 g, 1.42 mmole) and benzoyl chloride (0.31 mL, 2.66 mmole) in 1,2-dichloroethane and the mixture was refluxed for 10.5 hours. The reaction was quenched with ice and the organic phase was washed sequentially with 2N HCI, water and 2N NaOH. Drying over CaCl2 and evaporation gave a solid that was purified by chromatography on silica gel eluted with pet. ether-ethyl acetate 5:1. Recrystallization from water:gave 0.32 g of pure product as yellow crystals, 82%. 1H NMR (CDCl3) δ: 1.6 (s, 3H, CH3), 2.23.(s, 3H, CH3), 2.24 (s, 3H, CH3), 7.4–7.6 (m, 5H, C6H5), 11.1 (br s, 1H, NH.) 13C NMR (CDCl3) δ: 12.4, 14.8, 23.6, 122.4, 124.7, 127.6, 128.3, 128.4, 131.9, 140.3, 146.4, 167.4, 195.0.

Workup

  1. temperaturethe mixture was refluxed for 10.5 hours
  2. customThe reaction was quenched with ice
  3. washthe organic phase was washed sequentially with 2N HCI, water and 2N NaOH
  4. dry with materialDrying over CaCl2 and evaporation
  5. customgave a solid
  6. customthat was purified by chromatography on silica gel
  7. washeluted with pet. ether-ethyl acetate 5:1
  8. customRecrystallization from water

Sources & evidence

ORD record
ord-e0d8dc7dcfd34d208988bca0034f5e02
Source dataset
uspto-grants-2006_03
Patent number
US07019027B2

Reaction notes

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