Potassium Iodide → 6-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

HRID 2198616Notes

Reaction equation

HRID 2198616 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]([C:14](=[O:25])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]Br)=[CH:17][CH:16]=3)=[C:12]([C:26]3[CH:31]=[CH:30][C:29]([O:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=3)[S:11][C:10]=2[CH:37]=1)(=[O:4])=[O:3].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.[I-].[K+].C([Cl:48])(=O)C>CO.CN(C)C=O>[ClH:48].[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]([C:14](=[O:25])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)=[CH:17][CH:16]=3)=[C:12]([C:26]3[CH:31]=[CH:30][C:29]([O:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=3)[S:11][C:10]=2[CH:37]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6367Acetyl chlorideHCID 31268PyrrolidineHCID 204790006-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-bromoethoxy)benzoyl]benzo[b]thiophene

Product 1

HCID 1317128666-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A 1.19 g. portion of the product of Example 30 above, 20 ml. of anhydrous dimethylformamide and 3.4 g. of freshly distilled pyrrolidine were added to a flask at 25°, and then 100 mg. of powdered potassium iodide was added and the mixture was stirred at ambient temperature for 1 hour. The mixture was then evaporated under vacuum, 25 ml. of saturated aqueous sodium bicarbonate was added, and the mixture was extracted twice with 25 ml. portions of ethyl acetate. The extract was washed five times with 20 ml. portions of aqueous sodium chloride, and was dried over magnesium sulfate and evaporated to a brown oil. The oil was dissolved in 25 ml. of hydrochloric acid in methanol, which had been prepared by addition of 10 ml. of acetyl chloride to 100 ml. of methanol under nitrogen at 0°. The mixture was then evaporated to dryness under vacuum, and the resulting foam was crystallized from denatured ethanol to provide 1.07 g. of crystals, m.p. 206°-207°.

Workup

  1. customThe mixture was then evaporated under vacuum, 25 ml
  2. additionof saturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted twice with 25 ml
  4. washThe extract was washed five times with 20 ml
  5. dry with materialportions of aqueous sodium chloride, and was dried over magnesium sulfate
  6. customevaporated to a brown oil
  7. dissolutionThe oil was dissolved in 25 ml
  8. customof hydrochloric acid in methanol, which had been prepared by addition of 10 ml
  9. customat 0°
  10. customThe mixture was then evaporated to dryness under vacuum
  11. customthe resulting foam was crystallized from denatured ethanol
  12. customto provide 1.07 g

Sources & evidence

ORD record
ord-64fd5b4036e3406892ccf211e9ded7c2
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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