Ethanethiol → HCID 18461158, compound

HRID 2303376Notes

Reaction equation

HRID 2303376 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18]C)[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:24]([F:37])[CH:23]=2)=[O:21])=[CH:5][CH:4]=1.[Al+3].[Cl-:39].[Cl-].[Cl-].CCS>C(Cl)Cl>[ClH:39].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)=[C:24]([F:37])[CH:23]=2)=[O:21])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18461153HCID 18461153, compound

Product 1

HCID 18461158HCID 18461158, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

960 mg (1.85 mmol) of [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]3-fluorophenyl]methanone was dissolved in 30 mL of methylene chloride and cooled to 0° C. and 2.5 g (18.5 mmol) of AlCl3 was added in portions over a 10 minute interval. To the reaction mixture was added 2.75 mL (37 mmol) of EtSH and the reaction was stirred for 15 minutes. The reaction was heated to reflux and allowed to proceed for 1.5 hours. The reaction was allowed to cool and quenched with 100 mL of ice water. The crude product precipitated out and was collected by decanting off the liquids. The solid was dissolved in 50 mL of MeOH and chromatographed on a silica gel column eluted with a solvent of MeOH-CHCl3 (1:9). The appropriate fractions were determined by tlc and combined. The combined fractions were evaporated to dryness in vacuo. The residue was dissolved in 25 mL of MeOH and precipitated by adding a MeOH-HCl solution until no more precipitate formed. The liquid was decanted off and the salt re-dissolved in a minimal amount of MeOH. Ether was then added and the product was allowed to crystallize at −20° C. This yielded 470 mg of the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. waitto proceed for 1.5 hours
  4. temperatureto cool
  5. customquenched with 100 mL of ice water
  6. customThe crude product precipitated out
  7. customwas collected
  8. customby decanting off the liquids
  9. dissolutionThe solid was dissolved in 50 mL of MeOH
  10. customchromatographed on a silica gel column
  11. washeluted with a solvent of MeOH-CHCl3 (1:9)
  12. customThe combined fractions were evaporated to dryness in vacuo
  13. dissolutionThe residue was dissolved in 25 mL of MeOH
  14. customprecipitated
  15. additionby adding a MeOH-HCl solution until no more precipitate
  16. customformed
  17. customThe liquid was decanted off
  18. dissolutionthe salt re-dissolved in a minimal amount of MeOH
  19. additionEther was then added
  20. customto crystallize at −20° C

Sources & evidence

ORD record
ord-4a46fab0115f462295f7b94bbf1aca3f
Source dataset
uspto-grants-2002_08
Patent number
US06432982B1

Reaction notes

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