Phenylacetyl chloride → HCID 21075900, compound

HRID 1373868Notes

Reaction equation

HRID 1373868 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12]([Br:16])=[C:11]([O:17][CH2:18][C:19]#[N:20])[CH:10]=[CH:9]3)=[CH:4][C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]1=2.[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Br:16][C:12]1[C:13]2[C:8](=[CH:7][C:6]([C:5]3[S:1][C:2]4[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=4[C:4]=3[C:32](=[O:33])[CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]=1[O:17][CH2:18][C:19]#[N:20]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chloride2×HCID 24287Tin tetrachloride2×HCID 21075902HCID 21075902, compound

Product 1

HCID 21075900HCID 21075900, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a 0° C. mixture of (6-benzo[b]thiophen-2-yl-1-bromo-naphthalen-2-yloxy)-acetonitrile (4.87 g, 12.4 mmol) in chloroform (250 mL) was added phenylacetyl chloride (2.0 mL, 15 mmol) and tin (IV) chloride (2.2 mL, 19 mmol). It was refluxed for five hours. During reflux, additional phenylacetyl chloride (2.0 mL, 15 mmol) and tin (IV) chloride (2.2 mL, 19 mmol) were added. The reaction mixture was then allowed to cool to ambient temperature and poured into ice water. It was diluted with additional chloroform and washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtrered and solvent evaporated. After stirring the residue in ether and filtering, the filtrate was concentrated and purified by flash chromatography using 25–45% methylene chloride in hexane and 100% methylene chloride as eluent and then further purified by HPLC using 86% acetonitrile (0.1% formic acid) as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 60° C. for one hour yielded the title compound as a hard amber gum (0.531 g, 8.36%); mass spectrum (+EI, [M+H]+) m/z 512/514. 1H NMR (500 MHz, DMSO-d6): δ8.30 (d, 1H, J=8.70 Hz), 7.74 (d, 1H, J=9.17 Hz), 7.85 (dd, 1H, J=8.70 Hz and 1.83 Hz), 8.21–8.25 (m,2H), 8.07–8.10 (m, 1H), 7.90–7.94 (m, 1H), 7.44–7.50 (m, 2H), 7.13–7.19 (m, 3H), 6.91–6.94 (m, 2H), 5.47 (s, 2H), 3.8 ppm (s, 2H). Elemental Analysis for C28H18BrO2S: Calcd: C, 65.63; H, 3.54; N, 2.73; Found: C, 65.48; H, 3.43; N, 2.35.

Workup

  1. temperatureIt was refluxed for five hours
  2. temperatureDuring reflux
  3. washwashed with water and brine
  4. dry with materialIt was then dried with anhydrous magnesium sulfate
  5. customsolvent evaporated
  6. filtrationfiltering
  7. concentrationthe filtrate was concentrated
  8. custompurified by flash chromatography
  9. customfurther purified by HPLC
  10. customEvaporating the solvent
  11. extractionextracting with ethyl acetate
  12. washwashing with water and brine
  13. dry with materialdrying with anhydrous magnesium sulfate
  14. filtrationfiltering
  15. concentrationconcentrating
  16. customdrying in vacuo at 60° C. for one hour

Sources & evidence

ORD record
ord-84f788926d7d451c8532667b17b9ce8b
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

Loading…