Hydrochloric Acid → HCID 21182750, compound

HRID 1387006Notes

Reaction equation

HRID 1387006 reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+:5].[S-]CC.[Na+].C[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[C:21]3[CH:36]=[CH:35][CH:34]=[CH:33][C:22]=3[S:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:19])=[CH:14][CH:13]=1.Cl>CN(C=O)C.O>[S-:3][CH2:1][CH3:2].[Na+:5].[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([C:20]2[C:21]3[CH:36]=[CH:35][CH:34]=[CH:33][C:22]=3[S:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:19])=[CH:16][CH:17]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 4459711Sodium ethanethiolateHCID 10667130HCID 10667130, compound

Product 2

HCID 4459711Sodium ethanethiolateHCID 21182750HCID 21182750, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A ˜0.5 M solution of sodium thioethoxide was prepared by adding ethanethiol (1.60 mL, 21.4 mmol) to a suspension of 60% NaH dispersion in mineral oil (769 mg, 19.2 mmol) in 40 mL of anhydrous DMF at 0° C. The ice bath was removed and the solution was stirred at room temperature for 30 min. The 0.5 M solution of sodium thioethoxide was then added dropwise to the solution of 4.00 g (10.7 mmol) of 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl 4-methoxyphenyl ketone in 10.0 mL of anhydrous DMF at room temperature. The reaction mixture was heated at 85° C. for 3 h, then allowed to cool to room temperature, and acidified with 20 mL of 1.0 N HCl. To this was added 200 mL of H2O and the mixture was extracted with EtOAc (3×400 mL). The combined organic layers were washed with 200 mL of brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by PrepLC (30% EtOAc in hexanes) to afford 3.017 g of the title compound (8.37 mmol, 78%) as a yellow foam.

Workup

  1. customThe ice bath was removed
  2. temperatureThe reaction mixture was heated at 85° C. for 3 h
  3. temperatureto cool to room temperature
  4. extractionthe mixture was extracted with EtOAc (3×400 mL)
  5. washThe combined organic layers were washed with 200 mL of brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by PrepLC (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-69bdad64d35f4670a95745f789492fc5
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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